6C-butylglucoses from glucuronolactone: Suppression of silyl migration during borohydride reduction of lactols by cerium (III) chloride: Inhibition of phosphoglucomutase

被引：16

作者：

Masaguer, CF

Bleriot, Y

Charlwood, J

Winchester, BG

Fleet, GWJ

机构：

[1] UNIV OXFORD,DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND

[2] UNIV LONDON,INST CHILD HLTH,DIV BIOCHEM & GENET,LONDON WC1N 1EH,ENGLAND

来源：

TETRAHEDRON | 1997年 / 53卷 / 44期

基金：

英国惠康基金; 英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4020(97)10012-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the epimeric 6C-butylglucoses from D-glucuronolactone is reported. The sodium borohydride reduction of two fully protected lactols is highly stereoselective but is accompanied by migration of a silyl protecting group; in the presence of cerium(III) chloride, there is little change in the stereoselectivity but the migration of the silyl group is suppressed. 6R-6C-Methylglucose and 6R-6C-butylglucose are both better inhibitors of phosphoglucomutase than their 6S epimers. (C) 1997 Elsevier Science Ltd.

引用

页码：15147 / 15156

页数：10

共 7 条

[1] The first example of a 6-C-aryl-D-glucose: Inhibition of glucokinase [J].