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.
Type de document :
Article dans une revue
Carbohydrate Research, Elsevier, 2014, 386, pp.99-105. 〈10.1016/j.carres.2014.01.006〉
Domaine :
Liste complète des métadonnées

https://hal.univ-lorraine.fr/hal-01494402
Contributeur : Srsmc Ul <>
Soumis le : jeudi 23 mars 2017 - 14:03:58
Dernière modification le : mercredi 24 octobre 2018 - 18:38:05

Identifiants

Collections

Citation

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〉

Partager

Métriques

Consultations de la notice

45