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
基金
英国工程与自然科学研究理事会; 英国惠康基金;
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
收藏
页码:15147 / 15156
页数:10
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