研究者詳細 - 花谷　正

論文 - 花谷　正

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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

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

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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.

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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

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