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Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2021

N-Glycosylation with Sulfoxide Donors for the Synthesis of Peptidonucleosides

Résumé

The synthesis of glycopyranosyl nucleosides modified in the sugar moiety is less frequently explored, notably because of a lack of a reliable method to glycosylate pyrimidine bases. Herein we report a solution in the context of the synthesis of peptidonucleosides. They were obtained after glycosylation of different pyrimidine nucleobases with glucopyranosyl donors carrying an azide group at the C4 position. A methodological study involving different anomeric leaving groups (acetate, phenylsulfoxide and ortho-hexynylbenzoate) showed that a sulfoxide donor in combination with trimethylsilyl triflate as the promoter led to the best yields.

Domaines

Chimie organique
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Dates et versions

hal-03292018 , version 1 (20-07-2021)

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Margaux Beretta, Emilie Rouchaud, Lionel Nicolas, Jean-Pierre Vors, Thomas Dröge, et al.. N-Glycosylation with Sulfoxide Donors for the Synthesis of Peptidonucleosides. Organic & Biomolecular Chemistry, 2021, ⟨10.1039/d1ob00493j⟩. ⟨hal-03292018⟩
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