Synthesis of a versatile tetrasaccharide of sialyl Le(x) and Le(x) antigens

Article abstract of DOI:10.1016/0040-4020(96)00759-4

Benzyl 4-O-[2,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-β-D-galactopyranosyl]2, 3,6-tri-O-benzyl-β-D-glucopyranoside (4) was synthesized from benzyl lactoside (2) via regioselective protection of 3'-OH with 4-methoxybenzyl group. Oxidative deprotection of 4 afforded the valuable acceptor. 5. The trisaccharide 7 was obtained through coupling of 5 and phenyl 2-deoxy-3,4,6-tri-O-acetyl-2-phthalimido-1-thio-β-D-glucopyranoside (6). The desired tetrasaccharide 1 was built up through fucosylation of the benzylidene derivative 11 obtained from 7.