Synthesis of sugar episulfides and olefins from via-diols via cyclic sulfates

Abstract

Cyclic sulfates of vic-diols are transformed in one-pot into sugar episulfides by treatment with potassium thioacetate or thiourea followed by reaction with sodium methoxide; reaction of these cyclic sulfates with potassium selenocyanate followed by treatment with sodium borohydride allows the synthesis of sugar olefins.