N-Glycosylation with sulfoxide donors for the synthesis of peptidonucleosides??

Organic & Biomolecular Chemistry Pub Date: 2021-04-14 DOI: 10.1039/D1OB00493J

Abstract

The synthesis of glycopyranosyl nucleosides modified in the sugar moiety has been less frequently explored, notably because of the 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.

Graphical abstract: N-Glycosylation with sulfoxide donors for the synthesis of peptidonucleosides
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