Three sialyl-Lexepitope analogs, which carry fucose and α-sialyl-(2→3)-galactose residues atO-2 andO-3,O-3 andO-2, andO-4 andO-6 positions of 1-deoxy-D-glucose backbone, respectively, have been synthesized. Glycosylation of 1,5-anhydro-4,6-O-benzylidene-D-glucitol (1) or 1,5-anhydro-6-O-benzoyl-2,3-di-O-benzyl-d-glucitol (4) prepared from 1,5-anhydro-d-glucitol, with methyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (5) using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter, afforded the corresponding fucosyl 1,5-anhydro-d-glucitol derivatives7, 8and9. Glycosylation of7, 8or10derived from9, with methylO-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-d-glyceroα-d-galacto-2-nonulopyranosylonate)-(2→3)-2,4,6-tri-O-benzoyl-1-thio-β-d-galactopyranoside (11) in the presence of DMTST gave the expected tetrasaccharide derivatives12, 16and20. Hydrolysis of the benzylidene group in12and16gave compounds13and17. Finally13, 17and20were transformed, by reductive removal of the benzyl groups,O-deacylation and subsequent hydrolysis of the methyl ester, into the sialyl-Lexepitope analogs15, 19and22, respectively.