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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

Abstract : 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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https://hal-normandie-univ.archives-ouvertes.fr/hal-02354798
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Submitted on : Tuesday, November 12, 2019 - 2:52:54 PM
Last modification on : Thursday, July 2, 2020 - 3:29:40 AM

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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, American Chemical Society, 2017, 82 (17), pp.9030-9037. ⟨10.1021/acs.joc.7b01493⟩. ⟨hal-02354798⟩

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