Synthesis of specifically deuteriated derivatives of D-galactose and D-galactosamine

Abstract

Simple and convenient methods for introducing deuterium label at C-3 and C-6 position of N-acetyl-D-galactosamine and D-galactose, respectively, are described. For the synthesis of 2-acetamido-2-deoxy-D-3-[²H] galactopyranose, benzyl 2-acetamido-2-deoxy-4,6-O-benzylidene-α-D-galactopyranoside was oxidized with dimethyl sulfoxide- acetic anhydride and the product was reduced with sodium borodeuteride to introduce the deuterium at C-3. After benzylidene reduction, the mixture was subjected to hydrogenolysis and purified by column chromatography. 1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside was oxidized followed by reduction with sodium borodeuteride and deprotection to yield D-6-[²H] galactose.