D-GLYCOPYRANOSYL PHENYLSULPHONES: ACYLATION OF THEIR LITHIATED ANIONS AND REDUCTIVE DESULFONYLATION OF THE RESULTING ACYLATED SULFONES. A SYNTHESIS OF α-D-GLYCOSIDES

Article abstract of DOI:10.1016/S0040-4039(00)95050-0

The lithiated anion of 3,4,6-tri-O-t-butyldimethylsilyl-2-deoxy-α,β-D-glucopyranosyl phenylsulfone reacts with dimethylcarbonate and various phenyl esters to give stable acylated products.Subsequent reductive lithiation leads to enolates which ungergo kin