STUDIES ON SELECTIN BINDING INHIBITORS - SYNTHESIS OF SIALYL-LEWIS-X AND SIALYL-LEWIS-A EPITOPE ANALOGS CONTAINING 2-ACETAMIDO DERIVATIVE OF N-METHYL-1-DEOXYNOJIRIMYCIN

Synthesis of sialyl-Lewis x (15) and sialyl-Lewis a (17) epitope analo gs containing the 2-acetamido derivative of N-methyl-1-deoxynojirimyci n has been achieved. A suitably protected 2-acetamido-1-deoxynojirimyc in derivative 5, prepared from 1-deoxynojirimycin via the epoxide inte rmediate 3, was successively coupled with methyl-1-thioglycosides of L -fucose (6) and alpha-sialyl-(2-->3)-D-galactose (9). The resulting te trasaccharides (10 and 13) were each converted, by reductive N-methyla tion and deprotection, into the desired epitope analogs.