Syntheses of difluorinated carbasugar phosphates from trifluoroethanol

Anderl, Timo and Audouard, Christophe and Miah, Afjal and Percy, Jonathan M. and Rinaudo, Giuseppe and Singh, Kuldip. (2009) Syntheses of difluorinated carbasugar phosphates from trifluoroethanol. Organic and Biomolecular Chemistry, 7 (24). pp. 5200-5206. ISSN 1477-0520 (https://doi.org/10.1039/b914068a)

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.

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• Item metadata

  Item type:	Article
  ID code:	35060
  Dates:	Date Event 2009 Published
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	24 Oct 2011 12:37
  Last modified:	08 Apr 2024 19:36
  URI:	https://strathprints.strath.ac.uk/id/eprint/35060