Novel synthesis of 1-thioglycopyranoses via thioiminium salts

Abstract

Methanolysis of a glycosylthioiminium salt, which was prepared from the reaction of acetohalogenosugar with thioacetamide, afforded the corresponding per-O-acetylated 1,2-trans-1-thioglycose in good yield after fractional crystallization. This synthetic method is very convenient in operation and proceeds without loss of acetyl groups, as the reaction is carried out under mild and neutral conditions.