Synthesis of 4,4-difluoroglycosides using ring-closing metathesis

J.M. Percy, C. Audouard, J. Fawcett, G.A. Griffith, S. Pintat, C.A. Smith

Research output: Contribution to journalArticle

44 Citations (Scopus)

Abstract

4-Deoxy-4,4-difluoro-glycosides have been synthesised for the first time via a direct sequence involving ring-closing metathesis and indium-mediated difluoroallylation with 1-bromo-1,1-difluoropropene in water. Two protecting group strategies were explored, one to allow protection of the primary C-6 hydroxyl group throughout the sequence, while the second was intended to allow deprotection after RCM and before dihydroxylation. The benzyl ether could be used in the first role, and pivaloyl is effective in the second. Dihydroxylations were highly stereoselective and controlled by the orientation of the glycosidic C-O bond.
Original languageEnglish
Pages (from-to)528-541
Number of pages14
JournalOrganic and Biomolecular Chemistry
Volume2
DOIs
Publication statusPublished - 2004

    Fingerprint

Keywords

  • ring-closing metathesis
  • 4-difluoroglycosides
  • dihydroxylations

Cite this

Percy, J. M., Audouard, C., Fawcett, J., Griffith, G. A., Pintat, S., & Smith, C. A. (2004). Synthesis of 4,4-difluoroglycosides using ring-closing metathesis. Organic and Biomolecular Chemistry, 2, 528-541. https://doi.org/10.1039/B313731G