Synthesis of C-4 and C-7 triazole analogs of zanamivir as multivalent sialic acid containing scaffolds

Research output: Contribution to journalArticle

40 Scopus citations

Abstract

The relative reactivities of C-4 and C-7 azides derived from zanamivir were compared in cycloaddition reactions with a panel of alkynes. All of the reactions proceeded efficiently with no observable differences between primary and secondary azides. Significant rate differences were observed between several members of the alkyne panel. Most notably, a trialkyne derived from a 1,3,5-triazine core underwent complete reaction within 4 h, whereas an analogous trialkyne with an all carbon aromatic core required 18 h. These results suggest that the triazine core serves as an internal catalyst.

Original languageEnglish (US)
Pages (from-to)1636-1650
Number of pages15
JournalCarbohydrate Research
Volume342
Issue number12-13
DOIs
StatePublished - Sep 3 2007

Keywords

  • C-4 Analog
  • C-7 Analog
  • Click
  • Zanamivir

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

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