Multigram syntheses of the disaccharide repeating units of chondroitin 4- and 6-sulfates

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• 作者：Jacquinet ; Jean-Claude ; Rochepeau-Jobron ; Laurence ; Combal ; Jean-Philippe
• 关键词：Oligosaccharide synthesis ; Chondroitin sulfates ; Glycosaminoglycans
• 刊名：Carbohydrate Research
• 出版年：1998
• 出版时间：December 31, 1998
• 年：1998
• 卷：314
• 期：3-4
• 页码：283-288
• 全文大小：104 K

文摘

The multigram syntheses of β--glucopyranosyluronic acid-(1→3)-2-acetamido-2-deoxy-4- and 6-O-sulfo--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-β--glucopyranosyluronate-(1→3)-2-acetamido-2-deoxy-α--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.