From D-glucuronic acid to L-iduronic acid derivatives via a radical tandem decarboxylation-cyclization.
Carbohydr Res
; 386: 99-105, 2014 Mar 11.
Article
em En
| MEDLINE
| ID: mdl-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.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Oligossacarídeos
/
Radicais Livres
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Glucuronatos
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Ácido Idurônico
Idioma:
En
Ano de publicação:
2014
Tipo de documento:
Article