Syntheses of difluorinated carbasugar phosphates from trifluoroethanol

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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)

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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.

ORCID iDs

Anderl, Timo, Audouard, Christophe, Miah, Afjal, Percy, Jonathan M. ORCID logoORCID: https://orcid.org/0000-0001-8636-2704, Rinaudo, Giuseppe and Singh, Kuldip.;
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