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Synthesis of fluorophosphonylated acyclic nucleotide analogues via copper(I)-catalyzed Huisgen 1-3 dipolar cycloaddition†
Sonia Amel Diab,Antje Hienzch,Cyril Lebargy,Stéphane Guillarme,Emmanuel Pfund,Thierry Lequeux
Organic & Biomolecular Chemistry Pub Date : 08/21/2009 00:00:00 , DOI:10.1039/B912724K
Abstract

Preparation of several acyclonucleosides containing both a difluoromethylphosphonate group and a triazole moiety is described starting from a difluorophosphonosulfide. The key step of the synthesis involves a copper(I)-catalyzed Huisgen 1-3 dipolar cycloaddition between difluorophosphonylated azides and propargylated nucleobases derived from thymine and 2-amino-6-chloropurine.

Graphical abstract: Synthesis of fluorophosphonylated acyclic nucleotide analogues via copper(I)-catalyzed Huisgen 1-3 dipolar cycloaddition
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