D-glycopyranosyl phenylsulfones: Acylation of their lithiated anions and reductive desulfonylation of the resulting acylated sulfones. A synthesis of α-D-C-glycosides

The lithiated anion of 3,4,6-tri-O-t-butyldimethylsilyl-2-deoxy-α,β-D-glucopyronosyl phenylsulfone reacts with dimethylcarbonate and various phenyl esters to give stable acylated products. Subsequent reductive lithiation leads to enolates which undergo kinetic protonation to afford selectively α-D-C-glucosides.