Synthesis of a dimeric Lewis X hexasaccharide derivative corresponding to a tumor-associated glycolipid |
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| Authors: | M Nilsson T Norberg |
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| Institution: | Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, Sweden. |
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| Abstract: | 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. |
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