Synthesis of two hyaluronic-acid-related oligosaccharide 4-methoxyphenyl glycosides having a β-D-glucuronic acid residue at the reducing end

Abstract

Synthesis of two hyaluronic-acid-related oligosaccharides, the 4-methoxyphenyl beta-glycosides of beta-D-GlcpA-(1->3)-beta-D-GlcpNAc-(1->4)-D-GlcpA and beta-D-GlcpA-(1->3)-beta-D-GlcpNAc-(1->4)-beta-D-GlcpA-(1->3)-beta-D-GlcpNAc-(1->4)-D-GlcpA, is described. D-Glucopyranosyluronic acid residues were obtained by selective oxidation at C6 of corresponding D-glucopyranosyl residues after construction of the oligosaccharide backbones, using pyridinium dichromate and acetic anhydride.