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
收藏
页码：183 / 186
页数：4
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