Novel epimerization of aromatic C-nucleosides with electron-withdrawing substituents with trifluoroacetic acid-benzenesulfonic acid using mild conditions

Yu Lin Jiang, James T. Stivers

Research output: Contribution to journalArticlepeer-review

Abstract

Trifluoroacetic acid and benzenesulfonic acid in dichloromethane at ambient temperature have been found to be efficient co-catalysts for the epimerization of C-nucleosides with electron-withdrawing substituents. This approach provides a convenient route to the β anomer of the nucleosides with high yields in the range 54-78%. Synthesis of the 3′-phosphoramidite of 2,4-difluorophenyl C-nucleoside suitable for solid-phase DNA synthesis is described.

Original languageEnglish (US)
Pages (from-to)4051-4055
Number of pages5
JournalTetrahedron Letters
Volume44
Issue number21
DOIs
StatePublished - May 19 2003

Keywords

  • Benzenesulfonic acid
  • C-nucleosides
  • Dichloromethane
  • Epimerization
  • Trifluoroacetic acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Novel epimerization of aromatic C-nucleosides with electron-withdrawing substituents with trifluoroacetic acid-benzenesulfonic acid using mild conditions'. Together they form a unique fingerprint.

Cite this