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Chemoselective Acylation of Nucleosides.

ABSTRACT: Acylated nucleoside analogues play an important role in medicinal chemistry and are extremely useful precursors to various other nucleoside analogues. However, chemoselective acylation of nucleosides usually requires several protection and deprotection steps due to the competing nucleophilicity of hydroxy and amino groups. In contrast, direct protecting-group-free chemoselective acylation of nucleosides is a preferred strategy due to lower cost and fewer overall synthetic steps. Herein, a simple and efficient chemoselective acylation of nucleosides and nucleotides under mild reaction conditions, giving either O- or N-acylated products respectively with excellent chemoselectivity is reported.

SUBMITTER: Tang Y

PROVIDER: S-EPMC9481663 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Chemoselective Acylation of Nucleosides.

Tang Yu Y Grange Rebecca L RL Engl Oliver D OD Miller Scott J SJ

Chemistry (Weinheim an der Bergstrasse, Germany) 20220726 52

Acylated nucleoside analogues play an important role in medicinal chemistry and are extremely useful precursors to various other nucleoside analogues. However, chemoselective acylation of nucleosides usually requires several protection and deprotection steps due to the competing nucleophilicity of hydroxy and amino groups. In contrast, direct protecting-group-free chemoselective acylation of nucleosides is a preferred strategy due to lower cost and fewer overall synthetic steps. Herein, a simple ...[more]

PMID: 35730928

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