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

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