Carbene-Mediated Quaternarization of the Anomeric Position of Carbohydrates: Synthesis of Allylic Ketopyranosides, Access to the Missing α-Gluco and β-Manno Stereoisomers, and Preparation of Quaternary 2-Deoxy 2-Acetamido Sugars - Normandie Université Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2017

Carbene-Mediated Quaternarization of the Anomeric Position of Carbohydrates: Synthesis of Allylic Ketopyranosides, Access to the Missing α-Gluco and β-Manno Stereoisomers, and Preparation of Quaternary 2-Deoxy 2-Acetamido Sugars

Kevin Mebarki
  • Fonction : Auteur
Floriane Heis
  • Fonction : Auteur
Antoine Yvan
  • Fonction : Auteur
Philippe Joosten
  • Fonction : Auteur
Kévin Mébarki
  • Fonction : Auteur

Résumé

Following our work on the C–H functionalization of carbohydrates by the 1,5 insertion of metal–carbenes, we report herein the robust and scalable conversion of sugar γ-lactones into highly valuable glycosides having a quaternary anomeric position substituted by an allyl chain ready for further functionalization. A divergent synthetic approach furthermore provided a straightforward access to ketopyranosides with a large chemo- and stereodiversity at position 2.

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Chimie
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Dates et versions

hal-02354798 , version 1 (12-11-2019)

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Kevin Mebarki, Marine Gavel, Floriane Heis, Antoine Yvan, Philippe Joosten, et al.. Carbene-Mediated Quaternarization of the Anomeric Position of Carbohydrates: Synthesis of Allylic Ketopyranosides, Access to the Missing α-Gluco and β-Manno Stereoisomers, and Preparation of Quaternary 2-Deoxy 2-Acetamido Sugars. Journal of Organic Chemistry, 2017, 82 (17), pp.9030-9037. ⟨10.1021/acs.joc.7b01493⟩. ⟨hal-02354798⟩
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