2022/06/28 更新

写真a

ハナヤ タダシ
花谷 正
HANAYA Tadashi
所属
教育推進機構 教授
職名
教授
外部リンク

学位

  • 学術博士 ( 岡山大学 )

研究キーワード

  • Synthetic Organic Chemistry

  • Carbohydrate Chemistry

  • Heterocyclic Chemistry

  • 合成有機化学

  • 糖質化学

  • 複素環化学

研究分野

  • ナノテク・材料 / 構造有機化学、物理有機化学

  • ライフサイエンス / 生物有機化学

学歴

  • 岡山大学   理学研究科   化学専攻

    1982年4月 - 1984年3月

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    国名: 日本国

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  • 岡山大学   理学部   化学科

    1978年4月 - 1982年3月

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    国名: 日本国

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経歴

  • 岡山大学教育推進機構 教授

    2022年4月 - 現在

  • 岡山大学全学教育・学生支援機構 教授

    2016年4月 - 2020年3月

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  • 岡山大学教育開発センター 教授

    2014年4月 - 2016年3月

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  • 岡山大学自然科学研究科 准教授

    2003年4月 - 2014年3月

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  • 岡山大学 機器分析センター 助教授

    1997年4月 - 2003年3月

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所属学協会

 

論文

  • Synthesis of biopterin and related pterin glycosides 査読

    Tadashi Hanaya, Hiroshi Yamamoto

    IUBMB Life   65 ( 4 )   300 - 309   2013年4月

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    担当区分:筆頭著者   記述言語:英語  

    Certain pterins having a hydroxyalkyl side chain at C-6 have been found as glycosidic forms in certain prokaryotes, such as 2'-O-(α-D-glucopyranosyl) biopterin from various kinds of cyanobacteria, and limipterin from a green sulfur photosynthetic bacterium. Synthetic studies on glycosides of biopterin and related pterins have been made in view of the structural proof as well as for closer examination of their biological activities and functions. The syntheses of these natural pterin glycosides have effectively been achieved, mostly through appropriately protected N2-(N,N- dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]pterin derivatives as glycosyl acceptors, and are reviewed here. © 2013 IUBMB Life.

    DOI: 10.1002/iub.1137

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  • Inclusion complexation of 4′,6‑diamidino‑2‑phenylindole (DAPI) with cucurbit[7]uril and cyclodextrins (native β‑, 2,6‑di‑O‑methylated β‑, and γ‑cyclodextrin): characteristic inclusion behavior and fluorescence enhancement 査読

    Y. Sueishi, S. Hagiwara, N. Inazumi, T. Hanaya

    J. Incl. Phenom. Macrocycl. Chem.   99 ( 3-4 )   209 - 216   2021年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:SPRINGER  

    Herein, we investigated the inclusion complexation of a fluorescent probe [4 ',6-diamidino-2-phenylindole (DAPI)] using various cyclodextrins (CDs) and cucurbit[7]uril (CB7). Using the continuous variation method, DAPI was found to form a 1:1 inclusion complex with CDs and CB7. H-1-NMR and 2D ROESY (H-1-H-1 rotating frame nuclear Overhauser effect) spectroscopy indicated that the inclusion of DAPI by the CDs and CB7 occurs via the encapsulation of the phenyl group and indole moiety of DAPI. The stability of the CB7 inclusion complex was higher than that of the CDs: the stability was attributed to the extra interaction formed between the dicationic dye (DAPI) and polar carbonyl groups at the portals of CB7. Furthermore, we determined the fluorescence quantum yield (phi) of the inclusion complexes. The phi values of DAPI were significantly enhanced upon its inclusion by CB7 and increased as the empirical solvent polarity parameter (E-T(30)) decreased. Based on these results, we concluded that the polarity of the microenvironment and protonation ability of the excited state of DAPI play important roles in emission efficiency.

    DOI: 10.1007/s10847-020-01042-6

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  • Comparative study of inclusion complexation of tetraalkylphosphonium and ammonium salts with cucurbit[7]uril 査読

    Y. Sueishi, S. Hagiwara, Y. Matsumoto, T. Hanaya

    J. Incl. Phenom. Macrocycl. Chem.   98   117 - 122   2020年

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  • Characterization of group‑inclusion complexations of rhodamine derivatives with native and 2,6‑di‑O‑methylated β‑cyclodextrins 査読

    Y. Sueishi, Y. Matsumoto, Y. Kimata, Y. Osawa, N. Inazumi, T. Hanaya

    J. Incl. Phenom. Macrocycl. Chem.   96 ( 3-4 )   365 - 372   2020年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:SPRINGER  

    The inclusion complexations of rhodamine derivatives with native and 2,6-di-O-methylated beta-cyclodextrins (beta-CD and DM-beta-CD) were studied spectrophotometrically. Rhodamine derivatives were shown to form 1:1 inclusion complexes with beta-CDs by the continuous variation method. The structures of the inclusion complexes were characterized by H-1-H-1 rotating frame nuclear Overhauser effect spectroscopy (ROESY) NMR measurements. It was found that native beta-CD encapsulates the xanthenyl ring of rhodamines into the cyclodextrin cavity, while DM-beta-CD forms two group-in complexes (phenyl-in and xanthenyl-in (bidirectional (bimodal) inclusion complexes)) with rhodamines bearing moderately bulky functional groups. Furthermore, we demonstrated the unique thermodynamics for the group-inclusion complex formation by DM-beta-CD. The quantum yields for the inclusion complexes of rhodamines were determined using a quantum measurement apparatus equipped with a half-moon unit. The results indicated that the cyclodextrin inclusion of rhodamines with the bulky amino substituents on the xanthenyl ring largely decreases the quantum yield values. Based on these results, the substituent effects on the fluorescence process for the cyclodextrin inclusion complexes of rhodamines were discussed. This study provides useful insights for the functional group recognition of native and modified beta-CDs.

    DOI: 10.1007/s10847-020-00979-y

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  • Characterization of inclusion complexation of various tetraalkylammonium chlorides with cucurbit[7]uril by external highpressure studies 査読

    Y. Matsumoto, N. Inazumi, T, Hanaya, Y. Sueishi

    J. Incl. Phenom. Macrocycl. Chem.   92 ( 1-2 )   205 - 210   2018年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:SPRINGER  

    The inclusion constants of tetraalkylammonium salts (ASs) with cucurbit[7]uril (CB[7]) were determined at high-pressures using methylene blue as a chemical indicator. CB[7] formed 1:1 inclusion complexes with ASs. We found a characteristic dependence of the alkyl chain substituents in ASs on the inclusion equilibrium, which was responsible for the formation of clathrate hydrates of the AS in bulk. Furthermore, we examined the effects of external high pressures on the CB[7] inclusion complexations of ASs having different alkyl chain lengths. Pressure dependence experiments allowed us to calculate the reaction volume (Delta V) upon inclusion; i.e., the volume change (Delta V (desolv)) accompanying desolvation around the guest molecules and the volume change (Delta V (repel)) caused by the water molecules repelled from the CB[7] cavity. The volumetric study for the inclusion of ASs with CB[7] showed that in the tetraheptylammonium ion, one arm (alkyl chain) was encapsulated in the CB[7] cavity, while in other ASs, two arms were located in the cavity. NMR measurements of the complexes and pressure-dependent studies provided unique information on the structures of the inclusion complexes of ASs with CB[7].

    DOI: 10.1007/s10847-018-0832-y

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  • A comparative study on inclusion complexation of substituted anilinonaphthalene sulfonic acids with 1,6,20,25-tetraaza[6.1.6.1]-paracyclophane and β-cyclodextrin 査読

    Y. Sueishi, A. Itoh, N. Inazumi, Y. Osawa, T. Hanaya

    J. Incl. Phenom. Macrocycl. Chem.   91 ( 1-2 )   1 - 7   2018年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:SPRINGER  

    The inclusion complexations of paracyclophane (CP44) and beta-cyclodextrin (beta-CD) with several anilinonaphthalene sulfonic acids (ANSs) have been characterized via the enhancement of fluorescence spectra upon inclusion. beta-CD and CP44 formed 1:1 inclusion complexes with ANSs, and the high stability of inclusion complexes of the latter was demonstrated. The thermodynamic parameters observed from the temperature dependence of the inclusion constants (van't Hoff analysis) showed that CP44 inclusion complexations with ANSs are enthalpy-driven. Furthermore, the structure of the inclusion complexes was discussed based on H-1- and 2D ROESY-NMR measurements. It was found that CP44 encapsulates the naphthalene moiety of ANSs. On the other hand, differences in the structures of the beta-CD inclusion complexes were observed for the 4-OH-substituted ANS. The molecular recognition for the inclusion of beta-CD was found to be sensitive compared with that of CP44. In addition, the local polarity inside the CP44 and beta-CD cavities was evaluated using ANSs as the fluorescence probe. Based on these results, we have suggested that the local polarity of ANSs in the hydrophobic cavities of CP44 and beta-CD plays an important role in quantum yield enhancement upon inclusion.

    DOI: 10.1007/s10847-018-0790-4

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  • Efficient Total Syntheses of Natural Neopterin Glycosides: Neopterin Glucronide and Solfapterin 査読

    T. Hanaya, K. Iwasaki, K, Saeki, T. Hattori

    Heterocycles   95   390 - 409   2017年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)  

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  • Inclusion complexation abilities of cucurbit[6]uril for various aromatic amines in the presence of alkali metal cations 査読

    Yusaku Honda, Tadashi Hanaya, Yoshimi Sueishi

    J. Incl. Phenom. Macrocycl. Chem.   88   253 - 257   2017年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:SPRINGER  

    The inclusion complexation of aromatic amines with cucurbit[6]uril (CB[6]) capped with alkali metal cations was studied spectrophotometrically. We showed that CB[6] capped with alkali metal cations forms a 1:1 inclusion complex with the aromatic amine guests (neutral organic molecules), independent of the length of guest molecules. The effects of salts on the inclusion constants of CB[6] in the presence of different alkali salts were examined and it was found that the inclusion constants increased in the order of alkali cation Cs+ < Na+ < K+, suggesting the interaction of amine guests with the capped alkali metal cation. Further, the structures of the inclusion complexation of aromatic amines with CB[6] were characterized by H-1 NMR measurements. Based on the results, the inclusion abilities of CB[6] capped with alkali metal cations are discussed.

    DOI: 10.1007/s10847-017-0727-3

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  • Influence of Counter Anions on Inclusion Complexation of p-Sulfonatocalix[6] arene with 1-Butyl-3-methylimidazolium Salts (Ionic Liquids) 査読

    Yusaku Honda, Shono Fujitani, Sho Tamaki, Naoya Inazumi, Tadashi Hanaya, Yoshimi Sueishi

    ZEITSCHRIFT FUR PHYSIKALISCHE CHEMIE-INTERNATIONAL JOURNAL OF RESEARCH IN PHYSICAL CHEMISTRY & CHEMICAL PHYSICS   230 ( 8 )   1153 - 1164   2016年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WALTER DE GRUYTER GMBH  

    Using the inclusion complexation of methylene blue with p-sulfonatocalix[ 6] arene (Calix-S6) as a chemical indicator, the association constants of inclusion complexes of Calix-S6 with visible-spectroscopically inert 1-butyl-3-methylimidazolium salts (ionic liquids (IL): counter anions BF4-, PF6-, and Cl-) were determined. It was found that the experimentally observed association constants of IL with Calix-S6 in a water-methanol mixture increased in the order of counter anion Cl- < BF4- < PF6-. The F-19 NMR signals of counter anions BF4- and PF6- shift upfield upon addition of Calix-S6. From the F-19 NMR chemical shifts, we suggested that Calix-S6 forms weak 1 : 1 complexes with the BF4- and PF6- anions. The binding constants and their thermodynamic parameters for the complexation of the BF4- and PF6- anions with Calix-S6 were evaluated in a water-methanol mixture (6 : 4 (V/V)) at 298 K:K-A = 26.2M (-1) for BF4- and 106 M-1 for PF6 (-). Based on the results, the characteristics for the complexation of the counter anions with Calix-S6 were discussed and the inclusion constants of Calix-S6 with the cationic ringmoiety of 1-butyl-3-methyl-imidazolium salts were determined.

    DOI: 10.1515/zpch-2015-0611

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  • Investigation of inclusion complexation of imidazolium and pyrrolidinium chlorides with water-soluble p-sulfonatocalix[6]arene: characteristic effects of external pressure, temperature, and substituents 査読

    Yoshimi Sueishi, Yusaku Honda, Shono Fujitani, Naoya Inazumi, Tadashi Hanaya

    J. Incl. Phenom. Macrocycl. Chem.   86   255 - 261   2016年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:SPRINGER  

    Using the inclusion complexation of methylene blue as a chemical indicator, the inclusion constants of imidazolium and pyrrolidinium chlorides (ionic liquids (IL)) with p-sulfonatocalix[6]arene (Calix-S6) were determined in a water-methanol mixture. In the inclusion of imidazolium chlorides, we found the characteristic inclusion constants, dependent on the length of the alkyl side chain. From the temperature effect on the inclusion, the differences in the inclusion interactions of imidazolium and pyrrolidinium ring moiety with the sulfonate groups of the Calix-S6's portal were observed. Further, from high-pressure studies on the inclusion complexation, the volume changes caused by the conformational changes of Calix-S6 and desolvation around the guest and host molecules upon inclusion were evaluated. Based on the results, we demonstrated that the volume change related to desolvation upon inclusion plays an important role in the reaction volume for the inclusion equilibrium of IL with Calix-S6. The structures of the inclusion complexes were established from 2D ROESY NMR measurements and a volumetric study of the inclusion complexation with p-sulfonated Calix-S6 having a flexible cavity was performed.

    DOI: 10.1007/s10847-016-0660-x

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  • Characteristically Steric Effects of Substituent on Bidirectional Inclusion Complexation of α-Substituted Phenyl-2,4,6-trimethoxybenzyl(t-butyl)nitroxides with β-Cyclodextrins 査読

    K. Miyazono, T. Hanaya, Y. Sueishi

    J. Incl. Phenom. Macrocycl. Chem.   83 ( 1-2 )   193 - 197   2015年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1007/s10847-015-0537-4

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  • Characteristic effects of substituent and external pressure on group- inclusion complexation with p-sulfonatocalix[8]arene and gamma-cyclodextrin 査読

    Keitaro Miyazono, Tadashi Hanaya, Yoshimi Sueishi

    HIGH PRESSURE RESEARCH   34 ( 3 )   337 - 344   2014年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:TAYLOR & FRANCIS LTD  

    By synthesizing unique nitroxide probes (alpha-substituted phenyl-2,4,6-trimethoxybenzyl(t-butyl) nitroxide), we have shown that p-sulfonatocalix[8]arene (Calix-S8) and gamma-cyclodextin (gamma-CD) form electron spin resonance spectroscopically separable group-inclusion complexes (alpha-substituted phenyl-in (R-in) and t-butyl-in complexes) and determined the group-inclusion constants of Calix-S8 and gamma-CD. Using nitroxide probes, we have examined the effects of substituent and external pressure on group-inclusion complexation with Calix-S8 and gamma-CD. Experiments on pressure dependence enabled us to calculate the reaction volume (Delta V) for R-in and t-butyl-in complex formations. Delta V for group-in complexation with Calix-S8 had negative values. In contrast, Delta V values for gamma-CD showed positive values, which is responsible for the repelled water molecules in the CD cavity. The characteristic pressure effects on group-in complexation suggest that group recognition by gamma-CD is sensitive when compared with that by Calix-S8.

    DOI: 10.1080/08957959.2014.947605

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  • Selective Preparation of 6- and 7-(Polyhydroxypropyl)pterins from Pentos-2-uloses 査読

    T. Hanaya, K. Ito

    Heterocycles   88   1491 - 1499   2014年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)  

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  • First synthesis of asperopterin A, an isoxanthopterin glycoside from Aspergillus oryzae 査読

    Tadashi Hanaya, Hiroshi Yamamoto

    PTERIDINES   24 ( 1 )   3 - 6   2013年6月

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:INT SOC PTERIDINOLOGY  

    The key precursor, N-2-(N,N -dimethylaminomethylene)-6-hydroxymethyl-8-methyl-3-[2-(4-nitrophenyl)ethyl]-7-xanthopterin (16) was efficiently prepared from 2,5-diamino-6-methylamino-3H-pyrimidin-4-one (5) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (12), followed by the protection of the pteridine ring. Glycosylation of 16 with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (18) in the presence of tin(IV) chloride yielded the corresponding beta-D-ribofuranoside. Successive removal of the protecting groups of the resulting D-ribofuranoside provided asperopterin A (4b).

    DOI: 10.1515/pterid-2013-0005

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  • SYNTHESIS OF 2-ACETAMIDO-2,5-DIDEOXY-5-PHOSPHORYL-D-GLUCOPYRANOSE DERIVATIVES: NEW PHOSPHA-SUGAR ANALOGS OF N-ACETYL-D-GLUCOSAMINE 査読

    Tadashi Hanaya, Masahiro Kawaguchi, Masakazu Sumi, Kazuo Makino, Keiko Tsukada, Hiroshi Yamamoto

    HETEROCYCLES   86 ( 2 )   1147 - 1165   2012年12月

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Starting with N-acetyl-D-glucosamine, methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-xylo-hexofuranosid-5-ulose (18) was prepared in 7 steps. The addition reaction of dimethyl phosphonate to 18, followed by deoxygenation of its 5-hydroxy group, provided the 5-deoxy-5-dimethoxyphosphoryl-D-glucofuranoside derivative (21a). The hydride reduction of 21a, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-glucosamine analog (23) having a phosphoryl group in the hemiacetal ring. This was converted into the per-O-acetylated N-acetyl-D-glucosamine phospha-sugar (25), while the same treatment of the 5-deoxy-5-dimethoxyphosphoryl-L-idose dimethyl acetal derivative (13b) afforded the N-acetyl-L-idosamine phospha-sugar (29).

    DOI: 10.3987/COM-12-S(N)69

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  • SYNTHETIC STUDIES ON NATURAL PTERIN GLYCOSIDES 招待 査読

    Tadashi Hanaya, Hiroshi Yamamoto

    HETEROCYCLES   85 ( 10 )   2375 - +   2012年10月

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    担当区分:筆頭著者   記述言語:英語   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Some pterins having various kind of sugars attached to the hydroxyalkyl side-chain at C-6 are known to occur in certain prokaryotes as exemplified by 2'-O-(alpha-D-glucopyranosyl)biopterin isolated from various kinds of cyanobacteria. A synthetic exploration of various types of glycosides of biopterin and related pterins has been undertaken owing to a marked interest in their physiological functions and biological activities as well as the structural proof of those natural products. This review summarizes our synthetic studies on natural pterin glycosides by employing the appropriately protected N-2-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]pterin derivatives as glycosyl accepters.

    DOI: 10.3987/REV-12-742

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  • FIRST SYNTHESIS OF A NATURAL ISOXANTHOPTERIN GLYCOSIDE, ASPEROPTERIN-A 査読

    Tadashi Hanaya, Kazumasa Ejiri, Hiroshi Yamamoto

    HETEROCYCLES   84 ( 2 )   801 - 813   2012年1月

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The key precursor, N-2-(N,N-dimethylaminomethylene)-6-hydroxymethy1-8-methyl-3[2-(4-nitrophenypethyl]-7-xanthopterin (9) was efficiently prepared from 2,5-diamino-6-methylam1no-3H-pyrimidin-4-one (3) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (11). The first synthesis of asperopterin-A (2b) was achieved by treatment of 9 with 1-O-acetyl-2,3,5-tri-O-benzoy1-beta-D-ribofuranose (15) in the presence of tin(IV) chloride, followed by removal of the protecting groups.

    DOI: 10.3987/COM-11-S(P)57

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  • AN EFFICIENT SYNTHESIS OF ANTIBIOTIC SF-2312 (3-DIHYDROXYPHOSPHORYL-1,5-DIHYDROXY-2-PYRROLIDONE) 査読

    Tadashi Hanaya, Chika Itoh

    HETEROCYCLES   82 ( 2 )   1675 - +   2011年3月

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    N-Benzyloxy-2-(diethoxyphosphoryl)pent-4-enamide (6) was prepared from ethyl diethoxyphosphorylacetate in a 3-step sequence. Oxidative cleavage of the terminal olefin of 6 with osmium tetroxide and sodium periodate afforded 1-benzyloxy-3-diethoxyphosphoryl-5-hydroxy-2-pyrrolidone (7). The first synthesis of racemic SF-2312 was achieved by treatment of 7 with trimethylsilyl bromide, followed by hydrogenolysis.

    DOI: 10.3987/COM-10-S(E)80

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  • First Synthesis of a Natural Neopterin Glycoside: 3’-O-(β-D-Glucopyranosyluronic acid)neopterin 査読

    T. Hanaya, T. Hattori, D. Takayama, H. Yamamoto

    Pteridines   21 ( 3 )   79 - 83   2010年9月

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)  

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  • Synthesis of 6-hydroxymethylpterin α- and β-D-glucosides 査読

    T. Hanaya, H. Baba, K. Ejiri, H. Yamamoto

    80   1013 - 1025   2010年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.3987/COM-09-S(S)78

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  • First Synthesis of Biopterin α-D-Glucoside 査読

    T. Hanaya, H. Baba, H. Yamamoto

    Heterocycles   77   747 - 753   2009年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.3987/COM-08-S(F)60

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  • First Synthesis of a representative, Natural Pterin Glycoside: 2’-O-(α-D-Glucopyranosyl)biopterin 査読

    T. Hanaya, H. Yamamoto, W. Pfleiderer

    Pteridines   20   36 - 41   2009年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)  

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  • NMR Spectroscopic Characterization of Inclusion Complexes of Hydroxy-substituted Naphthalenes with Native and Modified β-Cyclodextrins 査読

    Y. Sueishi, N. Inazumi, T. Hanaya

    J. Incl. Phenom. Macrocycl. Chem.   64 ( 1-2 )   135 - 141   2009年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1007/s10847-009-9545-6

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  • Synthetic Studies on Pterin Glycosides: the First Synthesis of 2’-O-(α-D-Glucopyranosyl)biopterin 査読

    T. Hanaya, H. Baba, H. Toyota, H. Yamamoto

    Tetrahedron   65   7989 - 7997   2009年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1016/j.tet.2009.07.043

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  • AN EFFICIENT SYNTHETIC ROUTE FOR A VERSATILE CILIAPTERIN DERIVATIVE AND THE FIRST CILIAPTERIN D-MANNOSIDE SYNTHESIS 査読

    Tadashi Hanaya, Hiroki Baba, Mitsunori Kanemoto, Hiroshi Yamamoto

    HETEROCYCLES   76   635 - 644   2008年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The key precursor, N(2)-(N,N-dimethylaminomethylene)-l'-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]ciliapterin (15) was efficiently prepared from D-xylose via an improved route. The first synthesis of 2'-O-(alpha-D-mannopyranosyl)ciliapterin (2c) was achieved by treatment of 15 with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannnopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups.

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  • Efficient total syntheses of natural pterin glycosides: limipterin and tepidopterin 査読

    T. Hanaya, H. Baba, H. Toyota, H. Yamamoto

    Tetrahedron   64 ( 9 )   2090 - 2100   2008年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1016/j.tet.2007.12.042

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  • An Efficient Synthesis of 2’-O-(β-D-Ribofuranosyl)biopterin 査読

    T. Hanaya, K. Torigoe, K. Soranaka, H. Fujita, H. Yamamoto, W. Pfleiderer

    Pteridines   19 ( 3 )   72 - 78   2008年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)  

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  • First synthesis of tepidopterin [2’-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-threo-biopterin]

    T. Hanaya, H. Baba, H. Yamamoto

    Carbohydr. Res.   342 ( 15 )   2159 - 2162   2007年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1016/j.carres.2007.06.017

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  • An efficient, one-pot synthesis of fosfomycin dialkyl esters from (R)-2-tosyloxypropanal

    Tadashi Hanaya, Yuichi Nakamura, Hiroshi Yamamoto

    HETEROCYCLES   74   983 - 989   2007年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    (R)-2-Tosyloxypropanal (4) was prepared from D-mannitol in a 7-step sequence (51% overall yield). Addition of dialkyl phosphonates to 4 in the presence of titanium isopropoxide and the subsequent treatment with DBU stereoselectively afforded, in one-pot, fosfomycin dimethyl (5a) and dibenzyl (5b) esters both in 58% isolated yield.

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  • Improved syntheses of D-ribo- and 2-deoxy-D-ribofuranose phospho sugars from methyl β-D-ribopyranoside 査読

    T. Hanaya, Y. Koga, H. Kawamoto, H. Yamamoto

    Heterocycles   73   581 - +   2007年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.3987/COM-07-S(U)34

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  • A new route for preparation of 2-deoxy-D-ribofuranose phospho sugar 査読

    Heterocycles   72   411 - 420   2007年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.3987/COM-06-S(K)28

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  • The First Chemical Synthesis of 6-Thio-D-fructopyranose via Methyl 6-Bromo-6-deoxy-1,3-O-isopropylidene-α-D-fructofuranose as a Key Intermediate 査読

    T. Hanaya, N. Sato, H. Yamamoto

    Heterocycles   71   517 - 522   2007年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)  

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  • Synthesis of 6- and 7-(1,2,3-trihydroxy-1,2-O-isopropylidenepropyl)pteridines and deoxygenation of their 3 '-hydroxy groups

    Tadashi Hanaya, Daisuke Takayama, Hiroshi Yamamoto

    HETEROCYCLES   70   355 - +   2006年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Treatment of 3,4-O-isopropylidene-L-threo-pentos-2-ulose (7) with 5,6-diamino-1,3-dimethyluracil (8) afforded 1,3-dimethyl-6-[(1R,2S)-1,2,3-trihydroxy-1,2-O-isopropylidenepropyl]lumazine (9a) and its 7-substituted isomer (9b). Deoxygenation of 3'-hydroxy groups of 9a,b was investigated in connection with a practical transformation of neopterin into biopterin.

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  • Synthesis of functionalized phospholane oxides and phosphorinane oxides from 1,4- and 1,5-di-O-mesyloxy compounds

    Tadashi Hanaya, Karsten Schurrle, Hiroshi Yamamoto

    HETEROCYCLES   69 ( 1 )   283 - +   2006年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Treatment of 1,4-di-0-mesyl-2,3-di-O-methyl-L-threitol (8b) with phenylphosphine in the presence of sodium hydride in DMSO, followed by the action of hydrogen peroxide, afforded 3,4-dimethoxy-1-phenylphospholane 1-oxide (7), while the same treatment of 1,5-di-O-mesyl-2,3,4-tri-O-methyl-mesoxylitol (11b) provided 2,3,4-trimethoxy-1-phenylphosphorinane 1-oxide (14).

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  • Novel preparation of a 2 '-O-acetyl-1 '-O-(4-methoxybenzyl)-L-biopterin derivative, a versatile precursor for a selective synthesis of L-biopterin glycosides

    Tadashi Hanaya, Hiroki Toyota, Hiroshi Yamamoto

    SYNLETT   ( 13 )   2075 - 2078   2006年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:GEORG THIEME VERLAG KG  

    L-Rhamnose was converted, over a 13-step-sequence, into 2'-O-acetyl-N-2-(N,N-dimethylaminomethylene)-1'-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]-L-biopterin, an appropriately protected precursor of 1'-O- and 2'-O-monoglycosyl-L-biopterin. Thus, the first selective synthesis of these L-biopterin glycosides was accomplished by treatment of the precursor with either DDQ or sodium methoxide, then with tetra-O-benzoyl-alpha-D-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the remaining protecting groups.

    DOI: 10.1055/s-2006-949620

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  • Differential effects of substituent and pressure on induced inclusion complexation of 6-O-alpha-D-glucosyl-beta-cyclodextrin with 4-substituted phenols

    Yoshimi Sueishi, Naoya Inazumi, Tatsuhiro Ide, Tadashi Hanaya

    JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY   54 ( 3-4 )   201 - 208   2006年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:SPRINGER  

    The inclusion complexation of 6-O-alpha-D-glucosyl-beta-cyclodextrin (G-beta-CD), in which the glucosyl side chain is introduced to beta-CD, with various kinds of phenols was studied spectrophotometrically at high pressures. The characteristic effects of substituent and pressure were found for the inclusion complexation of G-beta-CD. The association constants K for the G-beta-CD inclusion complexation increased with an increase in the bulkiness of the 4-substituent groups in phenols. As the external pressure increases, the inclusion constants for the G-beta-CD complexation increased and the reaction volumes were estimated to be -3.8 to -19.4 cm(3) mol(-1) from their pressure dependences. From analysis of the effect of pressure on the inclusion complexation with G-beta-CD, the number of water molecules included in the G-beta-CD cavity in water was estimated. The number of water molecules repelled from the CD cavity plays an important role in the change in volume upon inclusion. In addition, the structures of the inclusion complexes of G-beta-CD with phenols have been established by 1D and 2D NMR measurements. Based on the results, we suggested that the ability of the G-beta-CD inclusion complexation is enhanced by the interaction between guest molecules and the glucosyl side chain of G-beta-CD.

    DOI: 10.1007/s10847-005-7368-7

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  • An efficient synthesis of 2 '-O-(beta-D-glucopyranosyl)- and 2 '-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-biopterins

    T Hanaya, K Soranaka, K Harada, H Yamaguchi, R Suzuki, Y Endo, H Yamamoto, W Pfleiderer

    HETEROCYCLES   67 ( 1 )   299 - 310   2006年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    N-2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1',2'-di-O-trimethylsilyl-L-biopterin (6) was prepared from L-biopterin in 5 steps. Glycosylation of 6 with 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl trichloroacetimidate (9) and 1,3,4,6-tetra-O-acetyl-2-phtalimido-beta-D-glucopyranose (10) respectively afforded the corresponding 2'-O-(beta-D-glucopyranosyl) derivatives (12b, 12c) as major products. Removal of protecting groups of 12c provided naturally occurring limipterin (2).

    DOI: 10.3987/COM-05-S(T)28

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  • Synthesis of phospholane 1-oxide having oxygen functional groups from a 4-bromobutylphoshinate derivative

    T Hanaya, S Kawase, H Yamamoto

    HETEROCYCLES   66   251 - 261   2005年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Ethyl 4-bromo-2,3-dimethoxybutyl(phenyl)phosphinate (10a) was prepared from 2,3-di-0-methyl-L-threitol (12) in five steps. Reduction of 10a with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrogen peroxide, afforded 3,4-dimethoxy-1-phenylphospholane I-oxide (3), while the reaction of 10a with magnesium in boiling THF resulted in the formation of ethyl 2-methoxy-3-butenyl(phenyl)phosphinate (26).

    DOI: 10.3987/COM-05-S(K)15

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  • An efficient synthesis of methyl 1,3-O-isopropylidene-alpha-D-fructofuranoside and 2,3 : 5,6-di-O-isopropylidene-D-glucose dimethyl acetal derivatives from sucrose

    T Hanaya, N Sato, H Yamamoto

    CARBOHYDRATE RESEARCH   340 ( 16 )   2494 - 2501   2005年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCI LTD  

    Acetalation of sucrose with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, followed by acetylation, afforded methyl 4,6-di-O-acetyl-1,3-O-isopropylidene-alpha-D-fructofuranoside and 4-O-acetyl-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal as major products, while tosylation of the intermediate acetals provided methyl 6-O-tosyl-1,3-O-isopropytidene-alpha-D-fructofuranose. (C) 2005 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.carres.2005.07.023

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  • Effects of pressure on inclusion complexation of methylene blue with water-soluble p-sulfonatocalix[n]arenes

    Y Sueishi, N Inazumi, T Hanaya

    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY   18 ( 5 )   448 - 455   2005年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:JOHN WILEY & SONS LTD  

    The effects of pressure were examined for the inclusion complexation of water-soluble p-sulfonated calix[n]arenes (Calix-Sn: n = 4, Calix-S4; n = 6, Calix-S6; n = 8, Calix-S8) with methylene blue (MB). A differential pressure effect was found in the inclusion equilibria of Calix-Sn. As the external pressure increases, the inclusion equilibrium of MB with Calix-S4 and Calix-S6 shifts to the dissociation side. However, with Calix-S8, the inclusion equilibrium shifts to the association side with increased pressure. From the pressure dependence of the inclusion equilibria of Calix-Sn, the reaction volumes, which are changes in volume accompanied by inclusion, were estimated as 32.1 cm(3) mol(-1) for Calix-S4, 30.1 cm(3) mol(-1) for Calix-S6 and -13.8 cm(3) mol(-1) for Calix-S8. In addition, the structures of the inclusion complexes of Calix-Sn with MB have been established by H-1 NMR measurements. Based on the results, the behavior of inclusion complexation with Calix-Sn is discussed. Copyright (c) 2004 John Wiley T Sons, Ltd.

    DOI: 10.1002/poc.888

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  • Synthesis and structural analysis of 6-deoxy-6-hydroxyphosphinyl-D-fructopyranose derivatives

    T Hanaya, K Imai, YV Prikhod'ko, H Yamamoto

    CARBOHYDRATE RESEARCH   340 ( 1 )   31 - 37   2005年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCI LTD  

    3,4-Di-O-benzyl-6-deoxy-6-diethoxyphosphinyl-1,2-O-isopropylidene-beta-D-fructofuranose (13) was prepared from the known 1,2-O-isopropylidene-6-O-tosyl-beta-D-fructofuranose in five steps. Reduction of 13 with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the 6-deoxy-6-hydroxyphosphinyl-D-fructopyranose derivative. This was converted into the 1,2,3,4,5-penta-O-acetyl-6-deoxy-6-methoxyphosphinyl-D-fructopyranoses, whose structure and conformation were established by H-1 NMR spectroscopy. (C) 2004 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.carres.2004.10.020

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  • Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (alpha-hydroxyphosphonates)

    T Hanaya, K Sugiyama, H Kawamoto, H Yamamoto

    CARBOHYDRATE RESEARCH   338 ( 16 )   1641 - 1650   2003年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCI LTD  

    The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/S0008-6215(03)00235-0

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  • Synthesis and structural analyses of 3-acetamido-1,4-di-O-acetyl-2,3,5-trideoxy-5-C(isopropylphosphinyl)-D-erythro-pentopyranoses

    T Oshikawa, K Seo, M Yamashita, T Hanaya, Y Hamauzu, H Yamamoto

    CARBOHYDRATE RESEARCH   338 ( 3 )   283 - 291   2003年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCI LTD  

    H-1 NMR spectroscopy of phosphorus containing hetero sugars (phospha sugars), revealed the alpha and beta configurations and chair conformations for 3-acetamido-1,4-di-O-acetyl-2,3,5-trideoxy-5-C-(isopropylphosphinyl)-alpha- and beta-D-erythro-pentopyranoses. The conformation of the title compounds was determined by H-1 NMR as C-1(4) in CDCl3 and the conformation was in accord with that in solid state determined by X-ray crystallographic analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0008-6215(02)00397-X

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  • Synthesis and structure analyses, of 1,2,4-tri-O-acetyl-3,5-di-deoxy-5-C-(isopropyl- and phenyl-phosphinyl)-D-erythro-pentopyranoses

    T Oshikawa, K Seo, M Yamashita, T Hanaya, Y Hamauzu, H Yamamoto

    HETEROCYCLIC COMMUNICATIONS   9 ( 6 )   559 - 566   2003年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:FREUND PUBLISHING HOUSE LTD  

    H-1 NMR spectroscopy for phosphorus containing hetero sugars (phospha sugars (9a-d) under bar and (17a-d) under bar) revealed the stereoisomeric configurations and the chair conformations for alpha - and beta -1,2,4-tri-O-acetyl-3.5-di-deoxy-5-C-(isopropyl- and phenyl-phosphinyl)-D-erythro-pentopyranoses. The conformations of the title compounds were characterized as C-4(1) chair form in CDCl3 by H-1 NMR (500 MHz), and the conformations were in accord with those in the solid state determined by X-ray crystallographic analyses.

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  • Synthesis of Sugar Analogs Having a Phosphorus Atom in the Pyranose Ring (Phospha Sugar) and Stereoselectivity of C-P Bond Introduction

    T. Hanaya, H. Yamamoto

    Trends in Heterocyclic Chemistry   9   1 - 18   2003年

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  • A new route for preparation of 5-deoxy-5-(hydroxyphosphinyl)-D-mannopyranose and -L-gulopyranose derivatives

    T Hanaya, H Yamamoto

    HELVETICA CHIMICA ACTA   85 ( 9 )   2608 - 2618   2002年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    Starting from methyl 2,3-O-isopropylidene-alpha-D-mannofuranoside (5), methyl 6-O-benzyl-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose (12) was prepared in three steps. The addition reaction of dimethyl phosphonate to 12, followed by deoxygenation of 5-OH group, provided the 5-deoxy-5-dimetltoxyphosphinyl-alpha-D-mannofuranoside derivative 15a and the beta-L-gulofuranoside isomer 15b. Reduction of 15a and 15b with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of HCl and then H2O2, afforded the D-mannopyranose (17) and L-gulopyranose analog 21, each having a phosphinyl group in the hemiacetal ring. These were converted to the corresponding 1,2,3,4,6-penta-O-acetyl-5-methoxyphosphinyl derivatives 19 and 23, respectively, structures and conformations (C-4(1) or C-1(4), resp.) of which were established by H-1-NMR spectroscopy.

    DOI: 10.1002/1522-2675(200209)85:9<2608::AID-HLCA2608>3.0.CO;2-F

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  • Synthesis of 5-deoxy-5-phosphinyl-D-galactopyranose derivatives: New phospha-sugar analogs of D-galactose

    T Hanaya, K Sugiyama, Y Fujii, A Akamatsu, H Yamamoto

    HETEROCYCLES   55 ( 7 )   1301 - +   2001年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The addition reaction of dimethyl phosphonate to 3,6-di-O-benzyl-1,2-O-isopropylidene-alpha -L-arabino-hexofuranos-5-ulose (11), followed by deoxygenation of 5-hydroxyl group, provided 5-deoxy-5-dimethoxyphosphinyl-D-galactofuranose derivative (13a). Reduction of 13a with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-galactopyranose analog (15) having a phosphinyl group in the hemiacetal ring. This was converted into the 1,2,4-tri-O-acetyl-5-methoxyphosphinyl derivatives (16), whose structure and conformation were established by H-1-NMR spectroscopy.

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  • A new route for preparation of 5-deoxy-5-hydroxyphosphinyl-D-gluco- and L-idopyranose derivatives

    T Hanaya, Y Fujii, S Ikejiri, H Yamamoto

    HETEROCYCLES   50 ( 1 )   323 - 332   1999年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    By starting with known 3,6-di-O-benzyl-1,2-O-isopropylidene-alpha-D-xylo-hexofuranos-5-ulose (5), the 3,6-di-O-benzyl derivatives (8 and 10) of the title phospho-sugar analogs were prepared in six steps through the key intermediates, 5-deoxy-5-dimethoxyphosphinyl- 1,2-O-isopropylidene-alpha-D-gluco- and -L-idofuranoses (7a and 7b), respectively. These products (8 and 10) were respectively converted into the corresponding 1,2,4-tri-O-acetyl-5-methoxyphosphinyl derivatives (9 and 11), whose structures and conformations (mostly in C-4(1)) were established by spectroscopy.

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  • Synthesis of 2-amino-2,5-dideoxy-5-hydroxyphosphinyl-D-mannopyranose derivatives: New phospho-sugar analogues of D-mannosamine

    T Hanaya, Y Fujii, H Yamamoto

    JOURNAL OF CHEMICAL RESEARCH-S   ( 12 )   790 - 791   1998年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:SCIENCE REVIEWS LTD  

    3,6-Di-O-benzyl-5-deoxy-5-dimethylphosphinyl-1,2-O-isapropylidene-alpha-D-glucofuranose 5 was converted, in four steps, into methyl 2-acetamido-3,6-di-O-benzyl-2,5-dideoxy-alpha-D-mannofuranoside which led to 3,5-di-O-benzyl derivatives 9 of a P-in-the-ring D-mannosamine analogue.

    DOI: 10.1039/a804961k

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  • Effect of a phosphorus atom upon vicinal H-1-H-1 coupling constants in pyranose derivatives having a C-P bond: Additivity rule for the effect of phosphorus substituents

    T Hanaya, H Yamamoto

    CARBOHYDRATE RESEARCH   306 ( 1-2 )   157 - 162   1998年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCI LTD  

    Additivity constants for phosphorus were estimated for the prediction of vicinal H-1-H-1 coupling constants by means of an additivity rule in a series of pyranose analogs having phosphorus as the ring heteroatom. The experimental J values were well reproduced by employing the proposed additivity constants with a small overall root-mean-square difference of 0.32 Hz. The prediction of coupling constants was employed for the investigation of conformational equilibria of pyranose analogs having a phosphinyl group in the ring or on the ring-carbon. (C) 1998 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0008-6215(97)10038-6

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  • Synthesis of 1'-O-, 2'-O- and 1',2'-Di-O-(beta-D-glucopyranosyl)-L-biopterin

    T Hanaya, K Soranaka, H Yamamoto, W Pfleiderer

    CHEMISTRY AND BIOLOGY OF PTERIDINES AND FOLATES 1997   49 - 52   1997年

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    記述言語:英語   掲載種別:研究論文(国際会議プロシーディングス)   出版者・発行元:BLACKWELL WISSENSCHAFTS-VERLAGGMBH  

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  • An Efficient Synthesis of Limipterin [2-O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-L-biopterin] via N2-(N, N-Dimethylamino)methylene-3-[2-(4-nitrophenyl)ethyl]-L-biopterin

    H. Yamamoto, T. Hanaya, K. Harada, H. Kawamoto, W. Pfleiderer

    Pteridines   7 ( 3 )   110 - 112   1996年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

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  • PTERIDINES .105. SELECTIVE N(3)-AND O(4)-ALKYLATION OF L-BIOPTERIN - A CONVENIENT SYNTHESIS OF 3-METHYL-L-BIOPTERIN AND O(4)-METHYL-L-BIOPTERIN AND THE VERSATILE N(2)-(N,N-DIMETHYLAMINOMETHYLENE)-N(3)-P-NITROPHENETHYL-PROTECTED L-BIOPTERIN

    T HANAYA, K TORIGOE, K SORANAKA, H YAMAMOTO, QZ YAO, W PFLEIDERER

    PTERIDINES   6 ( 1 )   1 - 7   1995年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:INT SOC PTERIDINOLOGY  

    Treatment of L-biopterin (1) with N,N-dimethyformamide dimethyl- (or diethyl)acetal and then with acetic anhydride in pyridine gave 1',2'-di-O-acetyl-N2-(N,N-dimethylaminomethylene)-L-biopterin (4), which was converted by the Mitsunobu reaction into 3-methyl (5) and 3-p-nitrophenetyl derivatives (7). The protective groups on the side chain diols and N2 of these compounds were selectively cleaved to furnish products 6, 8-10, among which 9 is naturally occurring 3-methyl-L-biopterin and 8 is N2,N(3)-protected biopterin, a versatile intermediate for various reactions on the side-chain diol. In contrast, the same Mitsunobu reactions of tri-N2:1',2'-O-acetyl-L-biopterin (11) afforded O4-methyl (12) and O4-NPE derivatives (13), both of which yielded O4-methyl-L-biopterin (14) and subsequently led to 4-amino-L-biopterin (18).

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  • Facile Formation of 2-Oxo-1,2-oxaphosphorinane from 1,4-Dihalo-2,3-dimethoxybutane : A New Preparative Route to a 1-Phosphono-pentopyranose(共著) 査読

    T HANAYA, A AKAMATSU, S KAWASE, H YAMAMOTO

    J. Chem. Res. (S)   194 - 195   1995年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)  

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  • Synthesis of 6-Amino-5,6-dideoxy-5-hydroxyphosphinyl-D-glucopyranose 査読

    T. Hanaya, Y. Fujii, H. Yamamoto

    Bull. Chem. Soc. Jpn.   67   2596 - 2599   1994年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1246/bcsj.67.2596

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  • Synthesis of 2''-O-and 1'', 2''-Di-O-(β-D-ribofuranosyl)-biopterin via N2-(N, N-Dimethylamino)methylene-3-(2-p-nitrophenethyl)-biopterin

    Pteridines   5   29 - 29   1994年

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  • Novel Stereoselective Preparation and Conformational Analysis of Furanose-Type Phosphono Sugar C-Glycosides (共著)

    Chem. Lett.   ( 1 )   93 - 96   1993年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1246/cl.1993.93

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  • N2-(N,N-DIMETHYLAMINOMETHYLENE)-O4-(2-P-NITROPHENYL-ETHYL)-BIOPTERIN - A VERSATILE INTERMEDIATE FOR A GLYCOSIDATION REACTION 査読

    H YAMAMOTO, T HANAYA, K TORIGOE, W PFLEIDERER

    CHEMISTRY AND BIOLOGY OF PTERIDINES AND FOLATES   338   21 - 24   1993年

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    記述言語:英語   掲載種別:研究論文(国際会議プロシーディングス)   出版者・発行元:PLENUM PRESS DIV PLENUM PUBLISHING CORP  

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  • ヘミアセタール環内にリン原子を有する糖類似体(リン糖)の合成 招待 査読

    T HANAYA, H YAMAMOTO

    有合化   51   377 - 387   1993年

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    担当区分:筆頭著者   記述言語:日本語   掲載種別:研究論文(学術雑誌)  

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  • Synthesis of 6-Deoxy-6-phenylphosphonoyl-D-fructopyranoses : The First Phosphorus-in-the-Ring Analogues of a Ketose (共著) 査読

    T. Hanaya, R. Okamoto, Y. V. Prikhod'ko, M.-A. Armour, A. M. Hogg, H. Yamamoto

    J. Chem. Soc. Perkin Trans. 1   1663 - 1671   1993年

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  • Stereoselectivity in the preparation of 5,6-dideoxy-5- dimethoxyphosphinyl-D- and -L-hexofuranoses, and an efficient synthesis of 5,6-dideoxy-5-hydroxyphosphinyl-L-galactopyranose (a P-in-the-ring L-fucose analogue) 査読

    T. Hanaya, K. Yasuda, H. Yamamoto, H. Yamamoto

    Bulletin of the Chemical Society of Japan   66   2315 - 2322   1993年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1246/bcsj.66.2315

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  • SYNTHESIS OF 2-AMINO-2,5,6-TRIDEOXY-5-PHENYLPHOSPHINYL-L-GALACTOPYRANOSE - THE P-IN-THE-RING ANALOG OF L-FUCOSAMINE 査読

    T HANAYA, H YAMAMOTO, H KAWAMOTO, MA ARMOUR, AM HOGG, H YAMAMOTO

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   65 ( 11 )   2922 - 2925   1992年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    3-O-Benzyl-1,2-O-isopropylidene-6-O-tosyl-alpha-D-allofuranose was led to methyl (5R and 5S)-3-O-benzyl-5, 6-dideoxy-5-[(methoxy)phenylphosphinyl]-D-ribo-hexofuranoside (9) in a 4 step sequence (55% overall yield). Methyl (5R and 5S)-2-acetamido-2,5,6-trideoxy-5-[(methoxy)phenylphosphinyl]-D-arabino-hexofuranoside (12) was prepared from 9 in 4 steps involving a C-2 inversion (62% overall yield). Compound 12 was then converted, in 2 steps, into the title compound, which was characterized as the peracetyl derivatives.

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  • ORIENTATION OF THE ADDITION OF DIMETHYL PHOSPHONATE TO 5,6-DIDEOXY-6-NITRO-D-HEX-5-ENOFURANOSES

    T HANAYA, H YAMAMOTO, H YAMAMOTO

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   65 ( 4 )   1154 - 1156   1992年4月

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    記述言語:英語   出版者・発行元:CHEMICAL SOC JAPAN  

    The addition of dimethyl phosphonate to six 5,6-dideoxy-6-nitro-D-hex-5-enofuranoses at 25-degrees-C in the presence of triethylamine preponderantly gave (5R)-adducts, whereas the same reaction at 100-degrees-C without a base yielded (5S)-adducts as the main products.

    DOI: 10.1246/bcsj.65.1154

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  • Synthesis of 2,4-Dideoxy-4-hydroxyphosphonoyl-D-erythro- and -L-threo-pentofuranoses (共著) 査読

    T. Hanaya, A. Noguchi, M.-A. Armour, A. M. Hogg, H. Yamamoto

    J. Chem. Soc. Perkin Trans. 1   295 - 301   1992年

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    担当区分:筆頭著者  

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  • X-RAY CRYSTAL-STRUCTURES OF 1,2,4-TRI-O-ACETYL-5-DEOXY-3-O-METHYL-5-[(S)-PHENYLPHOSPHINYL]-ALPHA-D-XYLOPYRANOSE AND ITS 5-[(S)-PHENYLPHOSPHINOTHIOYL] DERIVATIVE, AND CONFORMATIONS OF D-XYLOPYRANOSE ANALOGS HAVING A C6H5P(=R) GROUP IN THE HEMIACETAL RING 査読

    T RICHTER, P LUGER, T HANAYA, H YAMAMOTO

    CARBOHYDRATE RESEARCH   222   11 - 21   1991年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCIENCE BV  

    X-ray crystallographic analyses are reported for the two title compounds (8 and 9), of which the former crystallized in two modifications (8a and 8b). In all three structures, the pyranose rings have the C-4(1) (D) conformation and the substituents at C-1 are axial and those at C-2-C-4 are equatorial. The phenyl rings are oriented equatorially with their planes nearly parallel to the axial P = R bond (R = O, S). The favored conformations of various PhP(= R)-in-ring D-xylopyranose acetates (R = O, S, lone-pair;8-19) in solution are discussed. The inclination of the equatorial P-phenyl group of the alpha- and beta-D-xylopyranose analogs 8-13 is similar to that observed in the solid, whereas the inclination of the axial phenyl ring of the P-5 epimers 14-19 is near 90-degrees with respect to the equatorial P = R bond.

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  • AN EFFICIENT SYNTHESIS OF 2,4-DIDEOXY-4-HYDROXYPHOSPHINYL-D-ERYTHRO-PENTOFURANOSE 査読

    Carbohydr. Res.   209   C9 - C12   1991年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)  

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  • Synthesis of 5,6-dideoxy-5-phenylphosphinyl-L-galactopyranoses. The P-in-Ring Sugar Analogs of L-Fucose (共著) 査読

    T. Hanaya, H. Yamamoto, T. Ohmae, H. Kawamoto, M.-A. Armour, A. M. Hogg, H. Yamamoto

    Bull. Chem. Soc. Jpn.   64   869 - 876   1991年

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    担当区分:筆頭著者  

    DOI: 10.1246/bcsj.64.869

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  • A CONVENIENT SYNTHESIS OF (2R)-1-AMINO-1-DEOXY-1-PHOSPHINYLGLYCEROLS 査読

    T HANAYA, A MIYOSHI, A NOGUCHI, H KAWAMOTO, MA ARMOUR, AM HOGG, H YAMAMOTO

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   63 ( 12 )   3590 - 3594   1990年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    2,3-O-Isopropylidene-D-glyceraldehyde reacts with dimethylphosphine oxide in the presence of triethylamine to give separable (1S,2R)- and (1R,2R)-l-dimethylphosphinylglycerol (65:35), from which the (1R) and (1S) title compounds are respectively derived via 1-O-mesyl and 1-azido derivatives. The corresponding 1-dimethoxyphosphinylglycerols are similarly prepared. Structural and conformational assignments of these products are made on the basis of the H-1 NMR data and [alpha]D values.

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  • SYNTHESIS OF 5-DEOXY-3-O-METHYL-5-PHENYLPHOSPHINYL-L-FUCOPYRANOSES - THE 1ST P-IN-RING SUGAR ANALOGS OF L-FUCOSE TYPE 査読

    T HANAYA, T OHMAE, H KAWAMOTO, H YAMAMOTO

    CHEMISTRY LETTERS   ( 8 )   1359 - 1360   1990年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

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  • A CONVENIENT SYNTHESIS OF 1,2,4-TRI-O-ACETYL-5-DEOXY-5-[(R)- AND (S)-ETHYLPHOSPHINO AND PHENYLPHOSPHINO]-3-O-METHYL-ALPHA,BETA-D-XYLOPYRANNOSES AND THEIR PHOSPHINOTHIOYL DERIVATIVES 査読

    T HANAYA, N SHIGETOH, H YAMAMOTO, MA ARMOUR, AM HOGG

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   63 ( 2 )   421 - 427   1990年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

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  • AN IMPROVED SYNTHESIS OF THE 5-DEOXY-5-(HYDROXYPHOSPHINYL)-D-GLUCOPYRANOSES, AND CRYSTAL-STRUCTURES OF 1,2,3,4,6-PENTA-O-ACETYL-5-DEOXY-5-[(R)-METHOXYPHOSPHINYL]-BETA-D-GLUCOPYRANOSE AND ITS 5-[(R)-ETHYLPHOSPHINYL] CONGENER 査読

    T RICHTER, P LUGER, T HANAYA, H YAMAMOTO

    CARBOHYDRATE RESEARCH   193   9 - 21   1989年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCIENCE BV  

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  • SYNTHESIS OF 5-DEOXY-5-[(R AND S)-METHYLPHOSPHINYL]-ALPHA, BETA-D-MANNO-PYRANOSES - THE 1ST P-IN-RING SUGAR ANALOGS OF D-MANNOSE TYPE 査読

    H YAMAMOTO, T HANAYA, K OHMORI, H KAWAMOTO

    CHEMISTRY LETTERS   ( 8 )   1471 - 1472   1989年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

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  • SYNTHESIS AND STRUCTURAL-ANALYSIS OF 4-DEOXY-4-(HYDROXYPHOSPHINYL AND PHENYLPHOSPHINYL)-D-RIBOFURANOSES

    T HANAYA, H YAMAMOTO

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   62 ( 7 )   2320 - 2327   1989年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    DOI: 10.1246/bcsj.62.2320

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  • SYNTHESIS OF 1,2,4-TRI-O-ACETYL-5-DEOXY-5-[(R,S)-ETHYL AND PHENYLPHOSPHINO]-3-O-METHYL-ALPHA,BETA-D-XYLOPYRANOSES AND AN EFFICIENT CONVERSION TO THE CORRESPONDING 5-(PHOSPHINOTHIOYL)-D-XYLOPYRANOSES 査読

    H YAMAMOTO, T HANAYA, N SHIGETOH, H KAWAMOTO, S INOKAWA

    CHEMISTRY LETTERS   ( 2 )   349 - 352   1989年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

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  • AN EFFICIENT SYNTHESIS OF 4-DEOXY-4-(HYDROXYPHOSPHINYL)-D-RIBOFURANOSES - THE 1ST D-RIBOFURANOSE ANALOGS HAVING HYDROXYPHOSPHINYL GROUP IN THE HEMIACETAL RING 査読

    H YAMAMOTO, T HANAYA, H KAWAMOTO, S INOKAWA

    CHEMISTRY LETTERS   ( 1 )   121 - 124   1989年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

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  • SYNTHESIS OF 2,4-DIDEOXY-4-[(S)-METHYLPHOSPHINYL]-ALPHA,BETA-D-ERYTHRO-PENTOFURANOSES AND 2,4-DIDEOXY-4-[(R)-CYCLOHEXYLPHOSPHINYL]-ALPHA,BETA-D-ERYTHRO-PENTOFURANOSES - THE 1ST P-IN-RING SUGAR ANALOGS OF 2-DEOXY-D-RIBOFURANOSE TYPE 査読

    H YAMAMOTO, A NOGUCHI, K TORII, K OHNO, T HANAYA, H KAWAMOTO, S INOKAWA

    CHEMISTRY LETTERS   ( 9 )   1575 - 1576   1988年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

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  • Synthesis and Structural Analysis of 5-Deoxy-5-[(RS)-ethylphosphinyl]-α, β-L-idopyranoses

    H. Yamamoto, T. Hanaya, H. Kawamoto, S. Inokawa

    J. Org. Chem.   53 ( 20 )   4790 - 4793   1988年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1021/jo00255a023

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  • SYNTHESIS AND STRUCTURAL-ANALYSIS OF 5-DEOXY-3-O-METHYL-5-C-[(R)-XYLDPYRANOSES AND (S)-PHENYLPHOSPHINOTHIOYL]-ALPHA AND BETA-D-XYLOPYRANOSES 査読

    T HANAYA, N SHIGETOH, H YAMAMOTO

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   61 ( 7 )   2499 - 2505   1988年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

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  • SYNTHESIS AND CHARACTERIZATION OF 5-DEOXY-3-O-METHYL-5-C-[(R) AND (S)-PHENYLPHOSPHINOTHIOYL)-ALPHA-D-XYLOPYRANOSES AND BETA-D-XYLOPYRANOSES - THE 1ST SUGAR ANALOG HAVING A PHOSPHINOTHIOYL GROUP IN THE HEMIACETAL RING 査読

    H YAMAMOTO, T HANAYA, N SHIGETOH, H KAWAMOTO, S INOKAWA

    CHEMISTRY LETTERS   ( 10 )   2081 - 2084   1987年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

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  • SYNTHESIS AND STRUCTURAL-ANALYSIS OF 5-DEOXY-5-C-(HYDROXYPHOSPHINYL)-XYLOPYRANOSE AND 5-DEOXY-5-C-(HYDROXYPHOSPHINYL)-GLUCOPYRANOSE 査読

    H YAMAMOTO, T HANAYA, H KAWAMOTO, S INOKAWA, M YAMASHITA, MA ARMOUR, TT NAKASHIMA

    JOURNAL OF ORGANIC CHEMISTRY   50   3516 - 3521   1985年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    DOI: 10.1021/jo00219a018

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  • SYNTHESIS AND THE STRUCTURAL-ANALYSIS OF 1,2,3,4-TETRA-O-ACETYL-5-DEOXY-5-C-[(R,S)-METHOXYPHOSPHINYL]-ALPHA,BETA-D-XYLOPYRANOSES 査読

    H YAMAMOTO, T HANAYA, S INOKAWA, M YAMASHITA, MA ARMOUR, TT NAKASHIMA

    Carbohydr. Res.   128   C5 - C8   1984年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

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  • FORMATION AND CHARACTERIZATION OF 5-C-[(R)-(1-ACETOXY-ETHENYL)PHOSPHINYL]-1,2,4-TRI-O-ACETYL-5-DEOXY-3-O-METHYL-BETA-D-XYLOPYRANOSE 査読

    H YAMAMOTO, T HANAYA, S INOKAWA, MA ARMOUR

    CARBOHYDRATE RESEARCH   124 ( 2 )   195 - 200   1983年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCI LTD  

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▼全件表示

書籍等出版物

  • Sugar Analogs containing Carbon-Phosphorus Bonds

    Studies in Natural Products Chemistry  1990年 

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MISC

  • RECENT TOPICS IN C-P COMPOUNDS CHEMISTRY

    H YAMAMOTO, T HANAYA

    NIPPON NOGEIKAGAKU KAISHI-JOURNAL OF THE JAPAN SOCIETY FOR BIOSCIENCE BIOTECHNOLOGY AND AGROCHEMISTRY   65 ( 10 )   1518 - 1520   1991年10月

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    記述言語:日本語   掲載種別:書評論文,書評,文献紹介等   出版者・発行元:JAPAN SOC BIOSCI BIOTECHN AGROCHEM  

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  • Synthesis and structural analysis of 5-deoxy-5-[(R)- and (S)- methylphosphinyl]-α,β-D-manno- and -L-gulopyranoses

    T. Hanaya, K. Ohmori, H. Yamamoto, M. A. Armour, A. M. Hogg

    Bulletin of the Chemical Society of Japan   63 ( 4 )   1174 - 1179   1990年

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    記述言語:英語  

    DOI: 10.1246/bcsj.63.1174

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講演・口頭発表等

  • First Synthesis of a Natural Pterin Glycoside, Microcystbiopterin B

    T. Hanaya, Y. Maeda, K. Iwasaki

    20th European Carbohydrate Symposium (Leiden, The Netherlands)  2019年 

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    開催年月日: 2019年6月30日 - 2019年7月6日

    記述言語:英語   会議種別:ポスター発表  

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  • First Total Synthesis of a Natural Pterin Glycoside, Cyanopterin

    T. Hanaya, Y. Maeda, K. Ejiri

    19th European Carbohydrate Symposium (Barcelona, Spain)  2017年 

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    開催年月日: 2017年7月2日 - 2017年7月6日

    記述言語:英語   会議種別:ポスター発表  

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  • 天然プテリングリコシドの合成研究:ソルファプテリンの合成

    2016年日本化学会中国四国支部大会  2016年 

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  • Syntheic Studies on Natural Neopterin Glycosides

    23th European Colloquium on Heterocyclic Chemistry  2016年 

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  • 天然プテリングリコシドの合成研究:シアノプテリンの合成

    2016年日本化学会中国四国支部大会  2016年 

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  • 1-及び3-メチルルマジン誘導体の合成研究

    第30回日本プテリジン研究会  2016年 

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  • 新規ニトロキシドプローブのβ-CDによる双方向錯体形成に及ぼす特異的立体効果

    2015年日本化学会中国四国支部大会  2015年 

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  • 天然プテリングリコシドの合成研究

    第29回日本プテリジン研究会  2015年 

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  • 1-及び3-メチル化された天然ルマジン誘導体の合成

    2015年日本化学会中国四国支部大会  2015年 

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  • ソルファプテリンの合成研究

    2015年日本化学会中国四国支部大会  2015年 

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  • シアノプテリンの合成研究:グリコシル供与体部の合成

    2015年日本化学会中国四国支部大会  2015年 

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  • L-イジトールの新規合成と抗生物質FR-33289合成への応用

    2014年日本化学会中国四国支部大会  2014年 

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  • 1-及び3-メチルルマジン誘導体の合成研究

    2014年日本化学会中国四国支部大会  2014年 

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  • シアノプテリンの合成研究:6-ヒドロキシメチルプテリンのグリコシル化

    2014年日本化学会中国四国支部大会  2014年 

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  • L-イジトールの合成とホスホン酸抗生物質FR-33289合成への応用

    第4回リン化合物討論会  2013年 

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  • 天然ネオプテリングリコシドの合成研究

    第27回日本プテリジン研究会  2013年 

     詳細を見る

  • シアノプテリンの合成研究:グリコシル供与体部の合成

    2012年日本化学会西日本大会  2012年 

     詳細を見る

  • ネオプテリングリコシドの合成研究

    2012年日本化学会西日本大会  2012年 

     詳細を見る

  • 6-置換及び7-置換プテリン誘導体の選択的合成

    2012年日本化学会西日本大会  2012年 

     詳細を見る

  • First Synthesis of a Natural Isoxanthopterin Glycoside, Asperopterin-A

    15th International Symposium on Pteridines and Folates  2012年 

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  • N-アセチル-D-グルコサミン型ホスファ糖の合成

    2012年日本化学会西日本大会  2012年 

     詳細を見る

  • D-グルコサミン型ホスファ糖の合成研究

    2011年日本化学会西日本大会  2011年 

     詳細を見る

  • シアノプテリンの合成研究

    2011年日本化学会西日本大会  2011年 

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  • 環状ヒドロキサム酸構造を有する抗生物質SF-2312の合成と構造決定

    第3回リン化合物討論会  2011年 

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  • D-グルコサミン構造を有するホスファ糖の合成研究

    第3回リン化合物討論会  2011年 

     詳細を見る

  • アスペロプテリン-Aの合成

    第25回日本プテリジン研究会  2011年 

     詳細を見る

  • ホスホン酸型抗生物質SF-2312の合成研究と構造決定

    2011年日本化学会西日本大会  2011年 

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  • 天然ネオプテリングリコシド類の合成研究

    2010年日本化学会西日本大会  2010年 

     詳細を見る

  • 6-ヒドロキシメチルプテリングリコシドの合成研究

    第1回日本プテリジン研究会  2010年 

     詳細を見る

  • ホスホン酸型抗生物質ホスホノトリキシンの合成研究

    2010年日本化学会西日本大会  2010年 

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  • ホスホン酸型抗生物質SF-2312の合成研究

    2010年日本化学会西日本大会  2010年 

     詳細を見る

  • 環式ヒドロキサム酸構造を有する抗生物質SF-2312の合成研究

    第29回C−P化合物研究会  2009年 

     詳細を見る

  • First Synthesis of a Representative, Natural Pterin Glycoside: 2’-O-(α-D-glucopyranosyl)biopterin

    14th International Symposium on Pteridines and Folates  2009年 

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  • ビオプテリン α-D-グルコシドの合成研究

    第23回Japan Pteridine Conference, 第17回Cytokine Neopterin Meeting連合研究発表会  2009年 

     詳細を見る

  • ネオプテリングリコシドの合成研究

    2009年日本化学会西日本大会  2009年 

     詳細を見る

  • 6-ヒドロキシメチルプテリングリコシドの合成研究

    2009年日本化学会西日本大会  2009年 

     詳細を見る

  • ビオプテリングリコシドの合成研究

    第29回C−P化合物研究会  2009年 

     詳細を見る

  • ビオプテリン α-D-グルコシドの合成

    2008年日本化学会西日本大会  2008年 

     詳細を見る

  • アスペロプテリンA,Bの合成

    2008年日本化学会西日本大会  2008年 

     詳細を見る

  • ホスホマシシン誘導体の新規合成

    2008年日本化学会西日本大会  2008年 

     詳細を見る

  • ビオプテリングリコシドの合成

    第38回複素環化学討論会  2008年 

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  • シリアプテリングリコシドの合成研究

    第21回Japan Pteridine Conference, 第15回Cytokine Neopterin Meeting連合研究発表会  2008年 

     詳細を見る

  • Efficient Total Syntheses of Natural Pterin Glycosides: Limipterin and Tepidopterin

    23rd European Colloquium on Heterocyclic Chemistry  2008年 

     詳細を見る

  • ホスホマイシン誘導体の新規合成

    第28回C-P化合物研究会  2007年 

     詳細を見る

  • プテリングリコシド(リミプテリン、テピドプテリン)の合成研究

    日本化学会第87春季年会  2007年 

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  • D-リボフラノース及び2-デオキシ-D-リボフラノース型ホスファ糖の合成研究

    日本化学会第87春季年会  2007年 

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  • L-threo-ビオプテリングリコシド(テピドプテリン)の合成研究

    第21回Japan Pteridine Conference, 第15回Cytokine Neopterin Meeting連合研究発表会  2007年 

     詳細を見る

  • L-threo-ビオプテリングリコシド類の合成

    2007年日本化学会西日本大会  2007年 

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  • 2-デオキシ-D-リボフラノース型ホスファ糖の新規合成

    2007年日本化学会西日本大会  2007年 

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  • アルキル置換およびベンゾアズレン類の合成

    2007年日本化学会西日本大会  2007年 

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  • An Efficient, Selective Synthesis of 1'-O- and 2'-O-(b-D-glucopyranosyl)-L-biopterin and Limipterin

    2nd International Conference on Heterocyclic Chemistry  2006年 

     詳細を見る

  • Synthetic Studies on Phospholane Oxides and Phosphorinane Oxides Having Oxygen Functional Groups

    2nd International Conference on Heterocyclic Chemistry  2006年 

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  • 1'-O-及び2'-O-グリコシル-L-ビオプテリンの選択的合成

    第20回Japan Pteridine Conference, 第14回Cytokine Neopterin Meeting連合研究発表会  2006年 

     詳細を見る

  • ビオプテリングリコシドの選択的合成

    2006年日本化学会西日本大会  2006年 

     詳細を見る

  • アルキル置換アズレン類の合成研究

    2006年日本化学会西日本大会  2006年 

     詳細を見る

  • D-フルクトピラノース骨格を有するホスファ糖、チオ糖、イミノ糖の合成

    第27回C-P化合物研究会  2005年 

     詳細を見る

  • スクロースを用いたD-フルクトフラノース誘導体の合成とヘテロ糖合成への応用

    2005年日本化学会西日本大会  2005年 

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  • 部分的に保護された新規L-ビオプテリン誘導体の合成とグリコシル化

    2005年日本化学会西日本大会  2005年 

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  • 1,2-ジヒドロキシプロピル側鎖を有するプテリジン誘導体の新規合成

    2005年日本化学会西日本大会  2005年 

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  • D-グルコサミンの環内にリン原子を有するホスファ糖の合成研究

    2005年日本化学会西日本大会  2005年 

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  • トロピリデンを母体とする炭素数12の多環状ポリエノンの合成

    2005年日本化学会西日本大会  2005年 

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  • 側鎖水酸基を部分的に保護したL-ビオプテリン誘導体の合成とグリコシル化

    第19回Japan Pteridine Conference  2005年 

     詳細を見る

  • アミノ置換基を有するジヒドロアズレノン類の合成研究

    2004年日本化学会西日本大会  2004年 

     詳細を見る

  • スクロースを用いたD-フルクトフラノース誘導体の合成

    2004年日本化学会西日本大会  2004年 

     詳細を見る

  • 2-デオキシ-D-リボフラノース型ホスファ糖の合成

    2004年日本化学会西日本大会  2004年 

     詳細を見る

  • 電解還元反応を用いる三環式化合物の合成研究

    2004年日本化学会西日本大会  2004年 

     詳細を見る

  • ジメチルジヒドロアズレノンの合成と反応

    2003年日本化学会西日本大会  2003年 

     詳細を見る

  • D-フルクトピラノース骨格を有するホスファ糖の合成

    2003年日本化学会西日本大会  2003年 

     詳細を見る

  • 5-ホスフィニルヘキソフラノースの5位水酸基の脱酸素化の立体選択性

    第25回C-P化合物研究会  2002年 

     詳細を見る

  • 5-ホスフィニルヘキソフラノース誘導体の5位水酸基の脱酸素化の立体選択性

    2002年日本化学会西日本大会  2002年 

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  • ビオプテリンのグリコシド誘導体:天然物及び類似体の合成研究

    第25回C-P化合物研究会  2002年 

     詳細を見る

  • 1C4立体配座を優先するリン糖誘導体の合成と構造解析

    第25回C-P化合物研究会  2002年 

     詳細を見る

  • リミプテリンの合成研究

    2002年日本化学会西日本大会  2002年 

     詳細を見る

  • N-Arylacetyl-N'-[3-(2-pyridyldithio)propanoyl]-alpha,omega-alkanediamineの合成研究

    2002年日本化学会西日本大会  2002年 

     詳細を見る

  • モノ及びジメトキシジヒドロアズレノン類の合成研究

    2002年日本化学会西日本大会  2002年 

     詳細を見る

  • 電解還元反応によるビシクロケトン類の合成研究

    日本化学会中国四国支部・同九州支部合同大会  2001年 

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  • α-ヒドロキシホスホネートの脱ヒドロキシル化の立体選択性とホスファ糖合成への応用

    日本化学会第79春季年会  2001年 

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  • ピラノース環内にリン原子を有するD-ガラクトトース誘導体の合成

    日本化学会中国四国支部・同九州支部合同大会  2001年 

     詳細を見る

  • α-ヒドロキシホスホネート誘導体の脱ヒドロキシル化によるD-マンノース型リン糖の合成研究

    日本化学会中国四国支部・同九州支部合同大会  2001年 

     詳細を見る

  • 1'-O-グリコシル L-ビオプテリン誘導体の合成研究

    日本化学会中国四国支部・同九州支部合同大会  2001年 

     詳細を見る

  • 芳香族アミノジアゾケトン類のRh触媒による分解反応

    日本化学会中国四国支部・同九州支部合同大会  2001年 

     詳細を見る

  • ビオプテリンのグリコシド誘導体:天然物および類似体の合成研究

    第24回C-P化合物研究会  2000年 

     詳細を見る

  • Phospha-sugars: A Pseudo-sugar having a Phosphorus Atom in the Hemiacetal Ring

    8th International Symposium on Natural Product Chemistry  2000年 

     詳細を見る

  • α-ヒドロキシホスホネートの脱酸素化の選択性とリン糖合成への応用

    第24回C-P化合物研究会  2000年 

     詳細を見る

  • 1C4立体配座を有する新規リン糖誘導体の合成と構造解析

    日本化学会第77秋季年会  1999年 

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  • フラノース環内にリン原子を有するD-リボフラノース誘導体の改良的合成

    日本化学会第76春季年会  1999年 

     詳細を見る

  • アミノアズレン誘導体の合成研究

    日本化学会第76春季年会  1999年 

     詳細を見る

  • Synthetic Studies of D-ribofuranose Analogs Having a Phosphorus Atom in the Hemiacetal Ring

    17th International Congress of Heterocyclic Chemistry  1999年 

     詳細を見る

  • ピラノース環内にリン原子を有する糖類似体(リン糖)の合成と構造解析

    第14回若手化学者のための化学道場  1998年 

     詳細を見る

  • 5-デオキシ-5-ヒドロキシホスフィニル-D-ガラクトピラノース誘導体の合成

    日本化学会第75秋季年会  1998年 

     詳細を見る

  • Synthetic Studies of Sugar Analogs Having a Phosphorus Atom in the Hemiacetal Ring

    17th European Colloquium on Heterocyclic Chemistry  1998年 

     詳細を見る

  • D-ガラクトピラノース型リン糖の合成

    第23回C-P化合物研究会  1998年 

     詳細を見る

  • リン原子を有するピラノース環のビシナル1H-1H結合へ及ぼすリン原子の効果

    第23回C-P化合物研究会  1998年 

     詳細を見る

  • 2-アミノ-2,5-ジデオキシ-5-ヒドロキシホスフィニル-D-マンノピラノース誘導体(マンノサミン型リン糖)の合成

    日本化学会第74春季年会  1998年 

     詳細を見る

  • Synthesis of 1'-O-, 2'-O- and 1',2'-Di-O-(b-D-glucopyranosyl)-L-biopterin

    11th International Symposium on Chemistry and Biology of Pteridines and Folates  1997年 

     詳細を見る

  • リン原子を有するピラノース誘導体におけるリン原子のビシナル1H-1H結合定数への影響(リン原子の置換基効果の加成則)

    日本化学会第72春季年会  1997年 

     詳細を見る

  • トロピリデン環を有するジアゾケトンを用いた多環状ポリエノンの合成

    日本化学会第72春季年会  1997年 

     詳細を見る

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担当授業科目

  • 合成糖質化学 (2021年度) 後期  - その他

  • 天然へテロ環化学 (2021年度) 後期  - 金1,金2

  • 情報処理入門1(情報機器の操作を含む) (2021年度) 第1学期  - 月3,木3

  • 有機化学7 (2021年度) 第3学期  - 月1,月2

  • 有機化学8 (2021年度) 第4学期  - 月1,月2

  • 有機合成化学1 (2021年度) 第3学期  - 水3,水4

  • 有機合成化学2 (2021年度) 第4学期  - 水3,水4

  • 自然科学入門2 (2021年度) 第2学期  - 火3,火4

  • 合成糖質化学 (2020年度) 後期  - その他

  • 天然へテロ環化学 (2020年度) 後期  - 金1,金2

  • 情報処理入門1(情報機器の操作を含む) (2020年度) 第1学期  - 月3,木3

  • 有機化学7 (2020年度) 第3学期  - 月1,月2

  • 有機化学8 (2020年度) 第4学期  - 月1,月2

  • 有機化学IV (2020年度) 3・4学期  - 月1,月2

  • 有機合成化学 (2020年度) 3・4学期  - 水3,水4

  • 有機合成化学1 (2020年度) 第3学期  - 水3,水4

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