Process for the preparation of organic oligosaccharides, corresponding to fragments of natural muco-polysaccharides, oligosaccharides obtained and their biological applications

来自掌桥科研

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公开/公告号：

EP0084999 A1

公开/公告日期：

05/19/1988

发明人：

M Petitou，JC Jacquinet，P Sinay，J Choay，JC Lormeau

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摘要：

(+1.2.82, 16.2.82, 28.5.82, 22.6.82(2), 2.7.82 6.8.82, 20.9.82(2)-FR-001575, 002526, 009392 010891/2, 011679, 013804, 015803/4)\¦Prodn. of oligosaccharides (I) contg. or corresponding to fragments of acidic mucopolysaccharides comprises reacting two cpds., consisting of (or terminated by) units A of glucosamine (esp. in the D form) and of units U of glucuronic acid (esp.D) or iduronic acid (esp. L). One of units A and U is an alcohol with the hydroxy gp. at 3,4 or 6 position (for A) or at 2,3 or 4 position (for U), while the other has an activated anomeric carbon, i.e. an atom carrying a gp. reactive with hydroxy to form a glycosyl ether bond. All atoms (except the activated one) carry protected hydroxy, amino, or carboxy gps.(or their precursors) and it is esp. pref. that several different protecting gps. are used. This allows various substits. to be introduced subsequently at various positions. Formation of the disaccharide (2-N-sulphate or (2-N-acetyl)-6-O-sulphate-D-glucosamine) (methyl D-glucuronic acid). Intermediate oligosaccharides formed in the process and similar cpds. in which 1-3 hydroxy gps. are deprotected during the reaction are new. (I) are esp. useful as antithrombotic agents and also as biological reactants. The process is very generally applicable, and gives very pure prods. with the required stereospecificity.

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