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Driving innovations in manufacturing: Open Access research from DMEM

Strathprints makes available Open Access scholarly outputs by Strathclyde's Department of Design, Manufacture & Engineering Management (DMEM).

Centred on the vision of 'Delivering Total Engineering', DMEM is a centre for excellence in the processes, systems and technologies needed to support and enable engineering from concept to remanufacture. From user-centred design to sustainable design, from manufacturing operations to remanufacturing, from advanced materials research to systems engineering.

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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

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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.