The Synthesis and Reactivity of Cyclic Thiocarbonates Derived From Some Carbohydrate 1,2-Diols

Abstract

The attempted synthesis of several carbohydrate 1,2-diols is reported, together with the transformation of two of these diols into cyclic thiocarbonates, namely 4,6-O-benzylidene-3-O-methyl-1,2-O-thiocarbonyl-a-D-glucose and 3,4-O-isopropylidene-1,2-O-thiocarbonyl-β-D-arabinose. The treatment of these thiocarbonates, and a furanose 1,2-thiocarbonate previously prepared by Mukaiyama, with methyl halides and with tributyltin hydride is discussed. A single-crystal X-ray diffraction study of 3,4-O-isopropylidene-1,2-O-thiocarbonyl-β-D-arabinose is recorded.