Synthesis of Natural and Sugar-Modified Nucleosides Using the Iodine/Triethylsilane System As -Glycosidation Promoter

Overview

Journal Int J Mol Sci

Publisher MDPI

Specialties Biochemistry
Chemistry
Molecular Biology

Date 2024 Aug 29

PMID 39201716

Authors

Martina Cimafonte

Anna Esposito

Maria De Fenza

Francesco Zaccaria

Daniele DAlonzo

Annalisa Guaragna

Affiliations

Soon will be listed here.

Abstract

The reagent system based on the combined use of EtSiH/I acts as an efficient -glycosidation promoter for the synthesis of natural and sugar-modified nucleosides. An analysis of reaction stereoselectivity in the absence of C2-positioned stereodirecting groups revealed high selectivity with six-membered substrates, depending on the nucleophilic character of the nucleobase or based on anomerization reactions. The synthetic utility of the EtSiH/I-mediated -glycosidation reaction was highlighted by its use in the synthesis of the investigational drug apricitabine.

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