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

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

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)7114-7122
Number of pages9
JournalJournal of Organic Chemistry
Volume82
Issue number14
DOIs
StatePublished - Jul 21 2017

Bibliographical note

Funding Information:
We are grateful to CNRS and the Ministere de l'enseignement superieur et de la recherche for financial support. We thank the Centre Regional des Mesures Physiques de l'Ouest (Universite de Rennes 1) for the registration of the mass spectra. This work was supported by the French Agence Nationale de la Recherche (ANR-10-BLAN-0718).

Fingerprint Dive into the research topics of 'Regioselective Galactofuranosylation for the Synthesis of Disaccharide Patterns Found in Pathogenic Microorganisms'. Together they form a unique fingerprint.

Cite this