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From D-glucuronic Acid to L-iduronic Acid Derivatives via a Radical Tandem Decarboxylation-Cyclization

Stéphane Salamone, Michel Boisbrun, Claude Didierjean, Yves Chapleur

Carbohydr Res. 2014 Mar 11;386:99-105.

PMID: 24508514

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP6556123 D-Glucuronic acid D-Glucuronic acid 6556-12-3 Price
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