Efficient synthesis of 6-substituted purine derivatives using Pd-catalyzed cross-coupling reactions with 2'-deoxyguanosine O6-tosylate

Fumi Nagatsugi, Yuki Ogata, Shuhei Imoto, Shigeki Sasaki

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

6-Substituted purine analogs function in a variety of biological activities including antiviral pathways. A number of studies have reported on the development of the efficient synthesis of these nucleoside analogs. We previously demonstrated that oligonucleotides containing 2-amino-6-vinylpurine derivatives react with the cytosine at the target site with extreme selectivity. This was the first finding that O6-tosylate derivative of guanosine worked as an efficient substrate for Pd(0)-catalyzed cross-coupling reaction with vinyltributylstannane to produce 2-amino-6-vinylpurine. In order to demonstrate usefulness of the tosylate precursor, in this study we investigated transition metal catalysts and ligands in achieving the cross-coupling reaction using boronic acids or Grignard reagents as a coupling partner.

Original languageEnglish
Pages (from-to)493-501
Number of pages9
JournalHeterocycles
Volume73
Issue numberC
DOIs
Publication statusPublished - Dec 1 2007

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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