Syntheses of α-linked derivatives of N-acetyl glucosamine and Gal-β(1-3)GalNAc (T antigen) directly with the natural N-acetyl protecting group

Abstract

α-Linked spacer arms, suitable for coupling on a protein carrier, have been introduced directly on GlcNAc and on Gal-β(1-3)GalNAc in a 1,2-cis fashion through a new procedure involving a completely stereoselective Michael addition of the anomeric sodium alcoholate onto β-tosyloxy acrolein prepared in situ from the sodium salt of malonaldehyde and tosyl chloride.