A simple access to the D-mannosidase inhibitor, 1-deoxymannojirimycin

被引：24

作者：

Spreitz, J ^{[1
]}

Stütz, AE ^{[1
]}

Wrodnigg, TM ^{[1
]}

机构：

[1] Graz Tech Univ, Inst Organ Chem, Glycogrp, A-8010 Graz, Austria

来源：

CARBOHYDRATE RESEARCH | 2002年 / 337卷 / 02期

基金：

奥地利科学基金会;

关键词：

1-deoxymannojirimycin; D-mannosidase inhibitor; open-chain ketose; 1,3,4,5-tetra-O-acetyl-6-bromo-6-deoxy-keto-D-fructose;

D O I：

10.1016/S0008-6215(01)00291-9

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Crystalline 1,3,4,5-tetra-O-acetyl-6-bromo-6-deoxy-keto-D-fructose was prepared by reaction of 1, 3,4,5-tetra-O-acetyl-D-fructopyranose with triphenylphosphane dibromide in dichloromethane. Subsequent deprotection followed by reaction of the free 6-bromodeoxyfructofuranose with sodium azide in N,N-dimethylformamide furnished the corresponding 6-azidodeoxyketose. Catalytic hydrogenation led to 1-deoxymannojirimycin in 27% overall yield from 1, 3,4,5-tetra-O-acetyl-D-fructopyranose. This access is simple, inexpensive, high-yielding and clearly suitable for multigram preparations. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：183 / 186

页数：4

共 25 条

[1] New entry for asymmetric deoxyazasugar synthesis: syntheses of deoxymannojirimycin, deoxyaltrojirimycin and deoxygalactostatin [J].

Asano, K ;

Hakogi, T ;

Iwama, S ;

Katsumura, S .

CHEMICAL COMMUNICATIONS, 1999, (01) :41-42

[2] CONCISE SYNTHESIS OF 1-DEOXYMANNOJIRIMYCIN [J].

BAXTER, EW ;

REITZ, AB .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (11) :1419-1422

[3] Crystalline chlorotetracetyl fructose and related derivatives [J].

Brauns, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1920, 42 :1846-1854

[4] A SIMPLE CONVERGENT SYNTHESIS OF THE MANNOSIDASE INHIBITOR 1-DEOXYMANNONOJIRIMYCIN FROM SUCROSE [J].

DERAADT, A ;

STUTZ, AE .

TETRAHEDRON LETTERS, 1992, 33 (02) :189-192

[5]

Elbein A. D., 1999, IMINOSUGARS GLYCOSID, p[216, 364]

[6] Synthesis of 6-deoxy-6-iodo-D-fructose [J].

Fellahi, M ;

Morin, C .

CARBOHYDRATE RESEARCH, 1999, 322 (1-2) :142-146

[7] A SHORT PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN FROM D-FRUCTOSE [J].

FURNEAUX, RH ;

TYLER, PC ;

WHITEHOUSE, LA .

TETRAHEDRON LETTERS, 1993, 34 (22) :3613-3616

[8]

Hamagashira N, 1996, J BIOCHEM-TOKYO, V119, P998

[9] Synthesis of D- and L-deoxymannojirimycin via an asymmetric aminohydroxylation of vinylfuran [J].

Haukaas, MH ;

O'Doherty, GA .

ORGANIC LETTERS, 2001, 3 (03) :401-404

[10] DARSTELLUNG VON ACETYLZUCKERN MIT FREIEM LACTOL-HYDROXYL UND SYNTHESE VON EINIGEN DISACCHARIDEN [J].

HELFERICH, B ;

STEINPREIS, R .

CHEMISCHE BERICHTE-RECUEIL, 1958, 91 (08) :1794-1798

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