PMID: 2114948Jun 1, 1990Paper

Syntheses of the methyl glycosides of the repeating units of chondroitin 4- and 6-sulfate

Carbohydrate Research
J C Jacquinet

Abstract

3,4,6-Tri-O-acetyl-D-galactal was transformed into methyl 6-O-acetyl-2-azido-4-O-benzyl-2-deoxy-beta-D-galactopyranoside and its 4-O-acetyl-6-O-benzyl analogue, each of which was glycosylated with activated, O-acetylated derivatives of methyl D-glucopyranosyluronate. The resulting beta-(1----3)-linked disaccharide derivatives were each reductively N-acetylated, hydrogenolysed, O-sulfated, and saponified to afford the disodium salts of methyl 2-acetamido-2-deoxy-3-O-(beta-D-glucopyranosyluronic acid)-4-O-sulfo-beta-D-galactopyranoside and the 6-O-sulfo analogue. D-Galactal was also transformed into activated derivatives of 2-azido-3,6-di-O-benzyl-2-deoxy-D-galactopyranose and their 3,4-di-O-benzyl analogues with various substituents at O-4 and O-6. These glycosyl donors were condensed with 6-O-protected derivatives of methyl 2,3-di-O-benzyl-beta-D-glucopyranoside to give the beta-(1----4)-linked disaccharide derivatives, which were selectively deprotected, then oxidised at C-6 of the gluco unit, reductively N-acetylated, selectively deprotected, O-sulfated at C-4 or C-6 of the galacto unit, and hydrogenolysed to give the disodium salts of methyl 4-O-(2-acetamido-2-deoxy-4-O-sulfo-beta-D-galactopyranosyl)-beta-D- glucopyranosidur...Continue Reading

Citations

Sep 3, 2002·Carbohydrate Research·Janusz MadajAndrzej Wiśniewski
May 21, 1999·Carbohydrate Research·J C JacquinetJ P Combal
Oct 21, 2005·Organic Letters·Ren-Hua FanAlexander Wei
May 20, 1998·Natural Product Reports·A V Stachulski, G N Jenkins
Sep 3, 2009·Case Reports in Medicine·Vikrant MittalRajesh R Tampi
Mar 15, 2015·Bioorganic & Medicinal Chemistry Letters·Masahiro WakaoYasuo Suda
Apr 14, 2005·Organic & Biomolecular Chemistry·John R HardingAndrew V Stachulski
Nov 17, 2012·Chemistry : a European Journal·Guillaume DesprasJean-Maurice Mallet
Jun 22, 2002·The Journal of Organic Chemistry·Carl S Rye, Stephen G Withers
May 15, 2018·The Journal of Organic Chemistry·Shuang YangPingsheng Lei
Dec 22, 2004·The Journal of Organic Chemistry·Shyam M ReleElliot L Chaikof
Oct 27, 2006·The Journal of Organic Chemistry·Kenneth M EngstromAndrew O Stewart

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