N-Glycosylation with sulfoxide donors for the synthesis of peptidonucleosides | Zendy

Margaux Beretta | Zendy; Emilie Rouchaud | Zendy; Lionel Nicolas | Zendy; JeanPierre Vors | Zendy; Thomas Dröge | Zendy; M. EsSayed | Zendy; JeanMarie Beau | Zendy; Stéphanie Norsikian | Zendy

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N-Glycosylation with sulfoxide donors for the synthesis of peptidonucleosides

Author(s) -

Margaux Beretta,

Emilie Rouchaud,

Lionel Nicolas,

JeanPierre Vors,

Thomas Dröge,

M. EsSayed,

JeanMarie Beau,

Stéphanie Norsikian

Publication year - 2021

Publication title -

organic and biomolecular chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.923

H-Index - 146

eISSN - 1477-0539

pISSN - 1477-0520

DOI - 10.1039/d1ob00493j

Subject(s) - chemistry , glycosylation , anomer , pyrimidine , sulfoxide , trimethylsilyl trifluoromethanesulfonate , nucleobase , trifluoromethanesulfonate , azide , trimethylsilyl , context (archaeology) , combinatorial chemistry , protecting group , moiety , stereochemistry , trimethylsilyl azide , organic chemistry , biochemistry , catalysis , dna , paleontology , alkyl , biology

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.

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