From d-glucuronic acid to l-iduronic acid derivatives via a radical tandem decarboxylation-cyclization

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• 作者：St茅phane Salamone ; Michel Boisbrun ; Claude Didierjean ; Yves Chapleur
• 关键词：l-Idose ; C-5 inversion ; Radical decarboxylation ; Radical cyclization
• 刊名：Carbohydrate Research
• 出版年：11 March, 2014
• 年：2014
• 卷：386
• 期：Complete
• 页码：99-105
• 全文大小：1026 K

文摘

A synthesis to l-iduronic derivatives, major components of heparin derived pentasaccharides was accomplished by formal inversion of configuration at C-5 of a d-glucuronic acid derivative through radical formation at C-5 using Barton decarboxylation followed by intramolecular radical addition on an acetylenic tether at O-4 giving exclusively a bicyclic sugar of l-ido configuration. Oxidation and ring opening of this bicyclic sugar led to a l-iduronate. This method opens the way to short syntheses of pentasaccharidic moiety of Idraparinux and congeners.