Highly Regioselective Ring Opening of Five-Membered Cyclic Sulfates with Lithium Azide: Synthesis of Azido Sugars

Abstract

Abstract Cyclic sulfates of sugar pyranoses are easily prepared from their corresponding diol derivatives by treatment with thionyl chloride and subsequent oxidation of the resulting cyclic sulfites. Ring opening of these cyclic sulfates with lithium azide proceeds smoothly and in a highly regioselective fashion to give, after mild acid hydrolysis of the generated sulfate group, valuable azido sugars.