One-pot synthesis of carbohydrate thionolactones from 1-thiosugars

Abstract

A general and efficient one-pot method for the synthesis of carbohydrate thionolactones from the corresponding 1-thiosugar is described involving the formation of an intermediate glycosyl S-tert-butyl thiosulfinate in situ by treatment of a thiol with commercially available tert-butylsulfinyl chloride in toluene at room temperature, followed by thermolysis. The method can also be used to generate reactive thioaldehydes and thioketones directly from thiols, which can be trapped in situ with a suitable diene.