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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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https://hal.univ-lorraine.fr/hal-01494402
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Submitted on : Thursday, March 23, 2017 - 2:03:58 PM
Last modification on : Friday, February 26, 2021 - 3:24:02 PM

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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, Elsevier, 2014, 386, pp.99-105. ⟨10.1016/j.carres.2014.01.006⟩. ⟨hal-01494402⟩

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