Rearrangement of α-D-glucopyranose 4-sulphonates to 1,4-anhydro-β-D-galactopyranoses

Abstract

α-D-Glucopyranose derivatives with a sulphonyl group at C-4 and an acetyl group at C-1 undergo rearrangement to 1,4-anhydro-β-D-galactopyranoses on treatment with sodium azide; the replacement of a terminal azide group by bromide on treatment with hydrogen bromide is reported.