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Synthesis of biopterin and related pterin glycosides 査読

Tadashi Hanaya, Hiroshi Yamamoto

IUBMB Life 65 ( 4 ) 300 - 309 2013年4月

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

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

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

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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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

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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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

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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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

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

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

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

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

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

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

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

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

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 2375 - 2390 2012年

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

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 84 801 - 813 2012年

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 1675 - 1683 2011年

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

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

Heterocycles 80 1013 - 1025 2010年

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 79 - 83 2010年

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

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

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

First Synthesis of Biopterin α-D-Glucoside 査読

T. Hanaya, H. Baba, H. Yamamoto

Heterocycles 77 747 - 753 2009年

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

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

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

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

Tadashi Hanaya, Yuichi Nakamura, Hiroshi Yamamoto

Heterocycles 74 983 - 989 2007年

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

(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 - 591 2007年

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

Heterocycles 72 411 - 420 2007年

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

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

T. Hanaya, H. Baba, H. Yamamoto

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

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

Tadashi Hanaya, Daisuke Takayama, Hiroshi Yamamoto

HETEROCYCLES 70 355 - 365 2006年

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

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 査読

Tadashi Hanaya, Karsten Schurrle, Hiroshi Yamamoto

Heterocycles 69 ( 1 ) 283 - 294 2006年

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

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 査読

Tadashi Hanaya, Hiroki Toyota, Hiroshi Yamamoto

SYNLETT 2075 - 2078 2006年

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

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

Heterocycles 67 299 - 310 2006年

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

Yoshimi Sueishi, Naoya Inazumi, Tatsuhiro Ide, Tadashi Hanaya

JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY 54 201 - 208 2006年

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

T Hanaya, S Kawase, H Yamamoto

Heterocycles 66 251 - 261 2005年12月

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

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 査読

T Hanaya, N Sato, H Yamamoto

Carbohydr. Res. 340 2494 - 2501 2005年11月

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：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 査読

Y Sueishi, N Inazumi, T Hanaya

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

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

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

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

T. Hanaya, H. Yamamoto

Trends in Heterocyclic Chemistry 9 1 - 18 2003年

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

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

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

Carbohydr. Res. 338 283 - 291 2003年

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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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

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 査読

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

Heterocycles 55 1301 - 1309 2001年

担当区分：筆頭著者,　責任著者記述言語：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 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

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

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

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 査読

T Hanaya, K Soranaka, H Yamamoto, W Pfleiderer

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

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

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

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

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

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

Synthesis of 1,2,3,4,6-Penta-O-acetyl-5-deoxy-phenylphsophonothioyl-D-glucopyranoses 査読

T. Hanaya, A. Akamatsu, T. Isono, H. Yamamoto

J. Chem. Res. (S) 434 - 435 1994年

NOVEL EFFICIENT SYNTHESIS AND STRUCTURAL-ANALYSIS OF FURANOSE-TYPE PHOSPHONO SUGARS 査読

M YAMASHITA, A YABUI, T OSHIKAWA, T HANAYA, H YAMAMOTO

Heterocycles 38 1449 - 1452 1994年

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

Chem. Lett. ( 1 ) 93 - 96 1993年1月

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

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

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

1663 - 1671 1993年

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

Synthesis of 5-Deoxy-5-hydroxyphosphinyl-D-mannopyranoses 査読

T. Hanaya, K. Hirose, H. Yamamoto

Heterocycles 36 2557 - 2564 1993年

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

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

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

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

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

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 ( 3 ) 869 - 876 1991年

担当区分：筆頭著者記述言語：英語出版者・発行元：The Chemical Society of Japan

1,2-O-Isopropylidene-3-O-methyl-6-O-tosyl-β-D-arabino-hexofuranos-5-ulose (9a) and its 3-O-benzyl congener (9b) were prepared from 1,2:5,6-di-O-isopropylidene-β-D-altrofuranose in 4 steps. Addition of methyl phenylphosphinate to 9a and 9b in the presence of DBU, followed by reduction with Raney Ni, afforded (5R and 5S)-5,6-dideoxy-1,2-O-isopropylidene-5-[(methoxy)phenylphosphinyl]-3-O-methyl-β-D-arabino-hexofuranose(11a) and 3-O-benzyl congener (11b), respectively. The latter compound (11b) was debenzylated to 3-O-unsubstituted hexofuranose 11d. By reduction with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by acid hydrolysis, these key intermediates 11a, 11b, and 11d provided the title L-fucoses 13 (together with a minor proportion of D-altropyranoses 14) having as phenylphosphinylidene group in place of the ring oxygen. Compounds 13 and 14 were converted into per-O-acetyl derivatives for structural and conformational analysis by spectroscopy.

DOI： 10.1246/bcsj.64.869

CiNii Article

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Synthesis of 6-Deoxy-4-O-methyl-6-phenylphosphinyl-D-fructopyranoses. The First P-in-the-Ring Analogs of a Ketose 査読

T. Hanaya, R. Okamoto, Y. V. Prikhod'ko, H. Yamamoto

Chem. Lett. 1439 - 1442 1991年

Synthesis of 5-Deoxy-5-phenylphosphino- and 5-Phenylphosphinyl-D-glucopyranoses. 査読

Hanaya Tadashi, Akamatsu Akihito, Kawamoto Heizan, Armour Margaret-Ann, Hogg Alan M., Yamamoto Hiroshi

Bull. Chem. Soc. Jpn. 64 ( 8 ) 2398 - 2401 1991年

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

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.

Web of Science

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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

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

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

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

Bull. Chem. Soc. Jpn. 63 ( 4 ) 1174 - 1179 1990年

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

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

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

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

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 121 - 124 1989年

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

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

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

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

J. Org. Chem. 53 4790 - 4793 1988年

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

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

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

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

Carbohydr. Res. 124 195 - 200 1983年

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