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

Org Biomol Chem. 2009 Nov 7;7(21):4481-90. doi: 10.1039/b912724k. Epub 2009 Aug 21.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Catalysis
  • Copper / chemistry*
  • Nucleotides / chemical synthesis*
  • Nucleotides / chemistry*
  • Organophosphonates / chemistry*

Substances

  • Alkynes
  • Nucleotides
  • Organophosphonates
  • Copper