S-(4-Methoxyphenyl) benzenethiosulfinate (MPBT) trifluoromethanesulfonic anhydride:: A convenient system for the generation of glycosyl triflates from thioglycosides

被引：82

作者：

Crich, D ^{[1
]}

Smith, M ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 25期

关键词：

D O I：

10.1021/ol006715o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The combination of S-(4-methoxyphenyl) benzenethiosulfinate (MPBT, 1) and trifluoromethanesulfonic anhydride forms a powerful, metal-free, thiophile which readily activates thioglycosides, via glycosyl triflates, at -60 degreesC in dichloromethane, in the presence of 2,6 di-tert-butyl-4-methylpyridine. The glycosyl triflates are rapidly and cleanly converted to glycosides, upon treatment with alcohols, in good yield and selectivity.

引用

页码：4067 / 4069

页数：3