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
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.
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页码:4067 / 4069
页数:3
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