Synthesis of (3S,4S)-statine and a related compound, (3S,4S)-AHPPA, from D-glucosamine as a chiral pool

被引：6

作者：

Shinozaki, K ^{[1
]}

Mizuno, K ^{[1
]}

Oda, H ^{[1
]}

Masaki, Y ^{[1
]}

机构：

[1] GIFU PHARMACEUT UNIV, GIFU 502, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1996年 / 69卷 / 06期

关键词：

D O I：

10.1246/bcsj.69.1737

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Biologically important threo-beta-hydroxy-gamma-amino acids, (3S,4S)-statine ((3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid) (1) and (3S,4S)-AHPPA (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid) (2), were synthesized starting from D-glucosamine (3) as a chiral pool. Two routes for the transformation of D-glucosamine to key intermediates, which are applicable to the synthesis of threo-beta-hydroxy-gamma-amino acids, were investigated. The successful route involved C(6)-carbon degradation and elimination of the C(4)-hydroxy group of D-glucosamine in 8 steps and 30% overall yield to furnish (4R,5S)-2-oxo-5-vinyloxazolidine-4-carbaldehyde dimethyl acetal (17), which has been utilized as a versatile intermediate for synthesizing the target compounds.

引用

收藏

页码：1737 / 1745

页数：9

相关论文

共 36 条

[1] A NEW APPROACH TO THE STEREOSPECIFIC SYNTHESIS OF A DIHYDROXYETHYLENE ISOSTERE [J].

ATSUUMI, S ;

NAKANO, M ;

KOIKE, Y ;

TANAKA, S ;

FUNABASHI, H ;

HASHIMOTO, J ;

MORISHIMA, H .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (12) :3460-3462

[2] CARBOCYCLIC COMPOUNDS FROM MONOSACCHARIDES .1. TRANSFORMATIONS IN THE GLUCOSE SERIES [J].

BERNET, B ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1979, 62 (06) :1990-2016

[3] NOVEL REAGENT SYSTEM FOR CONVERTING A HYDROXY-GROUP INTO AN IODO-GROUP IN CARBOHYDRATES WITH INVERSION OF CONFIGURATION [J].

GAREGG, PJ ;

SAMUELSSON, B .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (22) :978-980

[4] PREPARATIVE AND EXPLORATORY CARBOHYDRATE CHEMISTRY - PROCEDURES FOR DIRECT REPLACEMENT OF PRIMARY HYDROXYL GROUPS IN CARBOHYDRATES BY HALOGEN [J].

HANESSIAN, S ;

PONPIPOM, MM ;

LAVALLEE, P .

CARBOHYDRATE RESEARCH, 1972, 24 (01) :45-+

[5] A SIMPLE PREPARATION OF 2-(ACYLAMINO)-2-DEOXY-3,4-5,6-DI-O-ISOPROPYLIDENE-ALDEHYDO-D-GLUCOSE DIMETHYL AND DIBENZYL ACETAL [J].

HASEGAWA, A ;

KISO, M .

CARBOHYDRATE RESEARCH, 1980, 79 (02) :265-270

[6] STUDIES ON AMINOSUGARS .28. SYNTHESIS OF BETA-L-IDOPYRANOSIDES THROUGH CORRESPONDING 5-ENOPYRANOSIDES [J].

IKEDA, D ;

TSUCHIYA, T ;

UMEZAWA, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1971, 44 (09) :2529-+

[7] LEWIS ACID-PROMOTED DIRECT SUBSTITUTION OF 4-METHOXY-2-OXAZOLIDINONES AND 4-PHENYLTHIO-2-OXAZOLIDINONES BY ALKYL CUPRATES - FACILE PREPARATION OF (3S,4S)-STATINE AND (3S,4S)-CYCLOHEXYLSTATINE [J].

ISHIBUCHI, S ;

IKEMATSU, Y ;

ISHIZUKA, T ;

KUNIEDA, T .

TETRAHEDRON LETTERS, 1991, 32 (29) :3523-3526

[8] OPTICALLY-ACTIVE N-PROTECTED ALPHA-AMINO ALDEHYDES IN ORGANIC-SYNTHESIS [J].

JURCZAK, J ;

GOLEBIOWSKI, A .

CHEMICAL REVIEWS, 1989, 89 (01) :149-164

[9]

KESSLER H, 1990, SYNTHESIS-STUTTGART, P457

[10] SYNTHESIS OF (3S, 4S)- AND (3S, 4R)-4-AMINO-3-HYDROXY-6-METHYLHEPTANOIC ACID, AND THEIR N-(ACETYL-L-VALYL-L-VALYL) DERIVATIVES [J].

KINOSHITA, M ;

HAGIWARA, A ;

ABURAKI, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1975, 48 (02) :570-575

← 1 2 3 4 →