Regioselective Galactofuranosylation for the Synthesis of Disaccharide Patterns Found in Pathogenic Microorganisms

Laurent Legentil; Yari Cabezas; Olivier Tasseau; Charles Tellier; Franck Daligault; Vincent Ferrières

doi:10.1021/acs.joc.7b00565

Regioselective Galactofuranosylation for the Synthesis of Disaccharide Patterns Found in Pathogenic Microorganisms

Laurent Legentil ¹ Yari Cabezas ¹ Olivier Tasseau ¹ Charles Tellier ² Franck Daligault ² Vincent Ferrières ¹

1 ISCR - Institut des Sciences Chimiques de Rennes

2 UFIP - Fonctionnalité et Ingénierie des Protéines

Abstract : Koenigs-Knorr glycosylation of acceptors with more than one free hydroxyl group by 2,3,5,6-tetrabenzoyl galactofuranosyl bromide was performed using diphenylborinic acid 2-aminoethyl ester (DPBA) as inducer of regioselectivity. High regioselectivity for the glycosylation on the equatorial hydroxyl group of the acceptor was obtained thanks to the transient formation of a borinate adduct of the corresponding 1,2-cis diol. Nevertheless formation of orthoester byproducts hampered the efficiency of the method. Interestingly electron-withdrawing groups on O-6 or on C-1 of the acceptor displaced the reaction in favor of the desired galactofuranosyl containing disaccharide. The best yield was obtained for the furanosylation of p-nitrophenyl 6-O-acetyl mannopyranoside. Precursors of other disaccharides, found in the glycocalix of some pathogens, were synthesized according to the same protocol with yields ranging from 45 to 86%. This is a good alternative for the synthesis of biologically relevant glycoconjugates.

Type de document :

Article dans une revue

Journal of Organic Chemistry, American Chemical Society, 2017, 82 (14), pp.7114-7122. 〈10.1021/acs.joc.7b00565〉

Domaine :

Chimie / Chimie organique

Liste complète des métadonnées

https://hal-univ-rennes1.archives-ouvertes.fr/hal-01578548
Contributeur : Laurent Jonchère <>
Soumis le : mercredi 13 septembre 2017 - 13:53:06
Dernière modification le : jeudi 5 avril 2018 - 10:36:59
Document(s) archivé(s) le : jeudi 14 décembre 2017 - 13:39:58

Regioselective Galactofuranosylation for the Synthesis of Disaccharide Patterns Found in Pathogenic Microorganisms

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Regioselective Galactofuranosylation for the Synthesis of Disaccharide Patterns Found in Pathogenic Microorganisms

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