Synthesis of n-octyl 2,6-dideoxy-α-l-lyxo-hexopyranosyl-(1→2)-3-amino-3-deoxy-β-d-galactopyranoside, an analog of the H-disaccharide antigen

Abstract The synthesis of an analog of the H-disaccharide antigen ( 2 ), in which the galactopyranosyl moiety bears an amino group at C-3 and the fucopyranosyl residue is deoxygenated at C-2, is reported. The key reaction in the preparation of 2 was the glycosylation of an appropriately protected n -octyl 3-azido-3-deoxy-galactopyranoside derivative with a 2,6-dideoxy thioglycoside promoted by 1-(phenylsulfinyl)piperidine and triflic anhydride. Disaccharide 2 is of interest in studies directed towards understanding the molecular basis of substrate recognition by the blood group A and B glycosyltransferases.