Direct conversion of 3,5,6-tri-O-benzoyl-1,2-O-isopropylidene-α-D-glucose into 4,5,6-tri-O-benzoyl-2,3-di-S-ethyl-2,3-dithio-D-allose diethyl dithioacetal

Abstract

The reaction of 3,5,6-tri-O-benzoyl-1,2-O-isopropylidene-α-D-glucose with ethanethiol in the presence of hydrogen chloride gives a crystalline product in 60% yield as was first described in 1932. This product is now shown to be 4,5,6-tri-O-benzoyl-2,3-di-S-ethyl-2,3-dithio-D-allose diethyl dithioacetal. A mechanistic outline for the reaction is proposed.