Stereoselective Reduction of 3-O-Hexofuranosyl S-Methyl Dithiocarbonates with Tributyltin Deuteride

Abstract

The reduction of several 3-O-hexofuranosyl (gluco, allo, galacto, gulo) S-methyl dithiocarbonates with tributyltin deuteride leads to highly stereoselective syntheses of 3-deoxy-[3-2H]hexofuranoses.Correspondingly, the reduction of the 3-O-[3-²H]hexofuranosyl (allo, gulo) S-methyl dithiocarbonates with tributyltin hydride leads to the epimeric (C3) 3-deoxy-[3-²H]hexofuranoses, and the reduction with tributyltin deuteride leads to the 3-deoxy-[3,3-2H₂]hexofuranose.