Click Azide-Alkyne Cycloaddition for the Synthesis of D-(-)-1,4-Disubstituted Triazolo-Carbanucleosides

Julie Broggi, Hiroki Kumamoto, Sabine Berteina-Raboin, Steven Patrick Nolan, Luigi A. Agrofoglio

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

A revisited and improved synthesis of an optically active azido-carbanucleoside is reported. This azido precursor is used in the successful and versatile synthesis of enantiomerically pure D-(-)-1,4-disubstituted 1,2,3-triazolo-carbanucleosides via copper(I)-catalyzed and microwave-assisted Huisgen 1,3-dipolar cycloaddition. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Original languageEnglish
Pages (from-to)1880-1888
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number12
DOIs
Publication statusPublished - Apr 2009

Keywords

  • Nucleosides
  • Carbanucleosides
  • Antiviral agents
  • Olefin metathesis
  • Huisgen cycloaddition
  • Ribavirin
  • Poxvirus
  • RING-CLOSING METATHESIS
  • CONJUGATE ADDITION-REACTION
  • REVERSED CYCLONUCLEOSIDE ANALOGS
  • S-ADENOSYLHOMOCYSTEINE HYDROLASE
  • L-CYCLOPENTENONE DERIVATIVES
  • ORTHOPOX VIRUSES SMALLPOX
  • CARBOCYCLIC NUCLEOSIDES
  • ANTIVIRAL ACTIVITY
  • PRACTICAL SYNTHESIS
  • ENANTIOSELECTIVE SYNTHESIS

Fingerprint

Dive into the research topics of 'Click Azide-Alkyne Cycloaddition for the Synthesis of D-(-)-1,4-Disubstituted Triazolo-Carbanucleosides'. Together they form a unique fingerprint.

Cite this