Syntheses of difluorinated carbasugar phosphates from trifluoroethanol

Timo Anderl, Christophe Audouard, Afjal Miah, Jonathan M. Percy, Giuseppe Rinaudo, Kuldip. Singh

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Difluorinated cyclohexene diols (prepd. from trifluoroethanol) can be elaborated to racemic analogs of phosphorylated sugars via regioselective protection and phosphorylation of the exposed C-1 hydroxyl group. Cis-diol protection was achieved using stannylene methodol., though the regioselectivity depended on the orientation of the Me group at C-5. UpJohn dihydroxylation is effective with the phosphotriester in place and global deprotection to the tetrol monophosphates I (R1 = OH, R2 = H; R1 = H, R2 = OH) is efficient.
Original languageUndefined/Unknown
Pages (from-to)5200-5206
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume7
Issue number24
DOIs
Publication statusPublished - 2009

Keywords

  • trifluoroethanol
  • difluorinated carbasugar phosphates
  • phosphorylated sugars
  • monophosphates

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