Synthesis of 2-deoxy-2-fluoro-glucotropaeolin, a thioglucosidase inhibitor

被引：21

作者：

Cottaz, S

Rollin, P

Driguez, H

机构：

[1] UNIV GRENOBLE 1,F-38041 GRENOBLE,FRANCE

[2] UNIV ORLEANS,INST CHIM ORGAN & ANALYT,F-45067 ORLEANS,FRANCE

来源：

CARBOHYDRATE RESEARCH | 1997年 / 298卷 / 1-2期

关键词：

glucosinolates; glucotropaeolin; thioglycosides; 2-deoxy-2-fluoro-glycosides; myrosinase; thioglucosidase inhibitor;

D O I：

10.1016/S0008-6215(96)00294-7

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：

S(N)2-Displacement of the anomeric bromine atom in 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-alpha-D-glucopyranosyl bromide with the tetrabutylammonium salt of triphenylmethanethiol afforded the corresponding trityl 1-thio-beta-D-glucoside which led to the fully protected S-acetyl-2-fluoro-1-thio-beta-D-glucose derivative, and then to the free thiol 5 by selective S-deacetylation at low temperature. 2-Fluoro-glucotropaeolin (1) was obtained by a conventional procedure from 5. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：127 / 130

页数：4

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