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1. Synthesis of the disaccharides methyl 4-O-(2?/3?-O-sulfo-?-d-glucopyranosyluronic acid)-2-amino-2-deoxy-?-d-glucopyranoside disodium salts, related to heparin biosynthesis

Author

Luigi Panza, Laura Cipolla, Francesco Nicotra, Ulf Lindahl, Luigi Lay, Giovanni Russo, Cipolla, L, Nicotra, F, Lay, L, Lindahl, U, Panza, L, and Russo, G

Subjects
Magnetic Resonance Spectroscopy, Heparin biosynthesis, Glycosylation, Molecular Structure, Heparin, Chemistry, Stereochemistry, Disaccharide, Alpha (ethology), Cell Biology, Nuclear magnetic resonance spectroscopy, Disaccharides, Biochemistry, heparin, disaccharides, chemistry.chemical_compound, Sulfation, Acetylation, CHIM/06 - CHIMICA ORGANICA, Molecule, Oxidation-Reduction, Molecular Biology, Chromatography, High Pressure Liquid
Abstract

The synthesis of the disaccharides methyl 4-O-(2'/3'-O-sulfo-beta-D-glucopyranosyluronic acid)-2-amino-2-deoxy-alpha-D-glucopyranoside 3 and 4 as disodium salts is described. Allyl 4,6-O-benzylidene-alpha-D-glucopyranoside 6 was converted to trichloroacetimidate 20. Glycosylation of 20 with 5 promoted by BF3 . OEt(2) gave disaccharide 21. Deacetylation of 21 followed by monoacetylation of the resultant diol 22 afforded the two monoacetylated disaccharides 23 and 24. Sulfation and deprotection of each disaccharide gave the desired sulfated compounds 3 and 4.

Published
1996
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