A CONVENIENT STRATEGY FOR REPLACEMENT OF THE ANOMERIC HYDROXYL GROUP BY DIFLUOROMETHYL FUNCTIONALITY IN CARBOHYDRATE-DERIVATIVES

J S HOULTON, W B MOTHERWELL, B C ROSS, M J TOZER, D J WILLIAMS, A M Z SLAWIN

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76 Citations (Scopus)

Abstract

A series of carbohydrate gem-difluoroenol ethers are readily prepared by the reaction of the corresponding lactones with dibromodifluoromethane, tris(dimethylamino)phosphine and zinc. Subsequent catalytic hydrogenation provides difluoromethyl C-glycoside analogues in which the exocyclic oxygen atom has been replaced by a difluoromethylene unit.

Original languageEnglish
Pages (from-to)8087-8106
Number of pages20
JournalTetrahedron
Volume49
Issue number36
Publication statusPublished - 3 Sept 1993

Keywords

  • NUCLEOSIDES
  • INHIBITORS
  • FLUORINE

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