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4′-Methoxyphenacyl-assisted synthesis of β-Kdo glycosides

Mazur Marcelina, Barycza Barbara, Andriamboavonjy Hanitra, Lavoie Serge, Tamigney Kenfack Marielle, Laroussarie Anaïs, Blériot Yves et Gauthier Charles. (2016). 4′-Methoxyphenacyl-assisted synthesis of β-Kdo glycosides. The Journal of Organic Chemistry, 81, (22), p. 10585-10599.

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3-Deoxy-β-d-manno-oct-2-ulosonic acid (β-Kdo) glycosides are mainly found in capsular polysaccharides and extracellular exopolysaccharides from Gram-negative bacteria. These compounds have profound biological implications in immune response and act as virulence factors. We have developed a novel methodology for the stereoselective synthesis of β-Kdo glycosides via the use of a 4′-methoxyphenacyl (Phen) auxiliary group at the C1 position of a peracetylated β-Kdo thioglycoside. Under the promotion of NIS/AgOTf in acetonitrile, a series of Kdo glycosides was synthesized in good yield and β-selectivity while minimizing the formation of undesirable glycals. Stereoselectivity of the glycosylation was shown to be modulated by various factors such as promotor, solvent, anomeric ratio of donor, nature of acceptor, and Phen substitution. Chemoselective cleavage of the Phen group was performed under the action of Zn/HOAc. DFT calculations together with experimental results suggested that α-triflate and a six-membered α-spiroPhen are plausible intermediates of the reaction, accounting for the enhanced formation of β-Kdo glycosides. The developed methodology could be applied to the synthesis of β-Kdo-containing glycans from pathogenic bacteria.

Type de document:Article publié dans une revue avec comité d'évaluation
Pages:p. 10585-10599
Version évaluée par les pairs:Oui
Identifiant unique:10.1021/acs.joc.6b01431
Sujets:Sciences naturelles et génie > Sciences naturelles > Chimie
Département, module, service et unité de recherche:Départements et modules > Département des sciences fondamentales
Mots-clés:Glycosides, synthesis, novel methodology, chemoselective cleavage
Déposé le:01 sept. 2021 19:04
Dernière modification:01 sept. 2021 19:04
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