A NOVEL 1,3 0-]C SILYL REARRANGEMENT IN CARBOHYDRATE-CHEMISTRY - SYNTHESIS OF ALPHA-D-GLYCOPYRANOSYLTRIMETHYLSILANES

被引:48
作者
PEDRETTI, V [1 ]
VEYRIERES, A [1 ]
SINAY, P [1 ]
机构
[1] ECOLE NORMALE SUPER,CHIM LAB,UA 1110,24 RUE LHOMOND,F-75230 PARIS 05,FRANCE
关键词
D O I
10.1016/S0040-4020(01)97585-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reductive lithiation of 2-O-trimethylsilyl derivatives of phenyl thiogluco and -galactopyranosides gives rise to a 13 O→C silyl migration leading to α-D-gluco and -galctopyranosyltrimethylsilanes in good yields. The expected β-elimination is observed to a small extent in the case of a 23-di-O-trimethylsilyl derivative of phenyl thioglucopyranoside where a tandem 13 O→C 14 O→O silyl rearrangement occurs but becomes the only possible reaction in the case of an O-silylated derivative of phenyl thiomannopyranoside. © 1990.
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页码:77 / 88
页数:12
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