Multigram syntheses of the disaccharide repeating units of chondroitin 4- and 6-sulfates.
The multigram syntheses of beta-D-glucopyranosyluronic acid-(1-->3)-2-acetamido-2-deoxy-4- and 6-O-sulfo-D-galactopyranose disodium salt, the disaccharide repeating units of chondroitin 4- and 6-sulfates, are described. The disaccharide benzyl methyl 2,3,4-tri-O-benzoyl-beta-D-glucopyranosyluronate- (1-->3)-2-acetamido-2-deoxy-alpha-D-galactopyranoside was used as a common intermediate. Selective benzoylation at O-6 followed by O-sulfonation at C-4 of the aminosugar moiety, saponification and catalytic hydrogenation afforded the 4-O-sulfo derivative, whereas selective O-sulfonation at C-6 followed by similar deprotection steps provided the 6-O-sulfo derivative in high yield.
Jacquinet
J C
JC
Institut de Chimie Organique et Analytique, UPRES-A CNRS 6005, U.F.R. Faculté des Sciences, Université d'Orléans, France. jean-claude.jacquinet@univ-orleans.fr
Rochepeau-Jobron
L
L
Combal
J P
JP
D002623:Chemistry Techniques, Analytical / Q000379:methods*; D002809:Chondroitin Sulfates / Q000138:chemical synthesis*; D004187:Disaccharides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical
D004187:Disaccharides; D002809:Chondroitin Sulfates