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Issue 24, 2009
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Syntheses of difluorinated carbasugar phosphates from trifluoroethanol

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Abstract

Difluorinated cyclohexene diols (prepared from trifluoroethanol) can be elaborated to racemic analogues of phosphorylated sugarsvia regioselective protection and phosphorylation of the exposed C-1 hydroxyl group. Cis-diol protection was achieved using stannylene methodology, though the regioselectivity depended on the orientation of the methyl group at C-5. UpJohn dihydroxylation is effective with the phosphotriester in place and global deprotection to the tetrol monophosphates is efficient.

Graphical abstract: Syntheses of difluorinated carbasugar phosphates from trifluoroethanol

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Publication details

The article was received on 14 Jul 2009, accepted on 21 Sep 2009 and first published on 20 Oct 2009


Article type: Paper
DOI: 10.1039/B914068A
Citation: Org. Biomol. Chem., 2009,7, 5200-5206
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    Syntheses of difluorinated carbasugar phosphates from trifluoroethanol

    T. Anderl, C. Audouard, A. Miah, J. M. Percy, G. Rinaudo and K. Singh, Org. Biomol. Chem., 2009, 7, 5200
    DOI: 10.1039/B914068A

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