Glycosylation with sulfoxide donors for the synthesis of peptidonucleosides

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 gl...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-05, Vol.19 (19), p.4285-4291
Main Authors: Beretta, Margaux, Rouchaud, Emilie, Nicolas, Lionel, Vors, Jean-Pierre, Dröge, Thomas, Es-Sayed, Mazen, Beau, Jean-Marie, Norsikian, Stéphanie
Format: Article
Language:
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. The activation of sulfoxide donors in the glycosylation of pyrimidine bases led efficiently to glycosylated adducts that were converted into peptidonucleosides, the analogues of gougerotin.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob00493j