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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

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