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Journal Articles Carbohydrate Research Year : 2014

From D-glucuronic acid to L-iduronic acid derivatives via a radical tandem decarboxylation-cyclization

Abstract

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.
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hal-01494402 , version 1 (23-03-2017)

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Stephane Salamone, Michel Boisbrun, Claude Didierjean, Yves Chapleur. From D-glucuronic acid to L-iduronic acid derivatives via a radical tandem decarboxylation-cyclization. Carbohydrate Research, 2014, 386, pp.99-105. ⟨10.1016/j.carres.2014.01.006⟩. ⟨hal-01494402⟩
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