AN EFFICIENT SYNTHESIS OF SULFO LEWIS X ANALOG CONTAINING 1-DEOXYNOJIRIMYCIN

Sulfo Lewis(x) analog containing 1-deoxynojirimycin (13) has been effi ciently synthesized. Glycosidation of ethyl 2,3,4-tri-0-benzyl-1-thio- beta-D-fucopyranoside (5) with isopropylidene-beta-D-galactopyranosyl) -(1-->4)-2, benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol (4), pr epared from O-beta-D-galactopyranosyl-(1-->4)-1,5-dideoxy-1, 5-imino-D -glucitol (1) via 3 steps, and subsequent acid hydrolysis of the isopr opylidene group gave the desired trisaccharide diol derivative (7) in good yield. Compound 7 was easily converted into 3'-O-sulfo Lewis(x) a nalog (13) via 6 steps in high yield.