Synthesis of a dimeric Lewis X hexasaccharide derivative corresponding to a tumor-associated glycolipid.
The dimeric Lewis X hexasaccharide p-trifluoroacetamidophenylethyl O-beta-D-galactopyranosyl-(1----4)-O-[alpha-L-fucopyranosyl-(1----3)]-O- (2- acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----3)-O-beta-D-galactopyrano syl- (1----4)-O-[alpha-L-fucopyranosyl-(1----3)]-2-acetamido-2-deoxy-beta-D- glucopyranoside (14), which is a derivative of a tumor-associated glycolipid, was synthesized from thioglycoside intermediates. A protected disaccharide was used as a key-intermediate for synthesis of the p-nitrophenylethyl glycoside of suitably protected O-beta-D-Galp-(1----4)-O-beta-D-GlcpN-(1----3)-O-beta-D-Galp-(1--- -4)-beta-D- GlcpN, which, after selective deblocking, was di-L-fucosylated and deprotected to give 14.
Nilsson
M
M
Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, Sweden.
Norberg
T
T
D014408:Biomarkers, Tumor; D006017:Glycolipids / Q000138:chemical synthesis*; D009844:Oligosaccharides / Q000138:chemical synthesis*
D014408:Biomarkers, Tumor; D006017:Glycolipids; D009844:Oligosaccharides