Further Aspects of the Reduction of Dithiocarbonates with Tributyltin Hydride and Deuteride

Abstract

The reduction of 1,2:5,6-di-O-isopropylidene-3-O-(methylthio) thiocarbonyl-β-D-idose ,- talose, and -(3-²H) talose with tributyltin hydride and deuteride leads to the deoxy sugar and some deuterium-containing deoxy sugars. A modification of the normal procedure allows for reduction with tributyltin hydride generated in situ. As well, the reduction of some dithiocarbonates derived from glycosides of N-acetyl-D- glucosamine allows access to a variety of dideoxy and trideoxy sugars.