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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.

Item type: Article
ID code: 35060
Notes: M1 - Copyright (C) 2011 American Chemical Society (ACS). All Rights Reserved. CAPLUS AN 2009:1472790(Journal)
Keywords: trifluoroethanol , difluorinated carbasugar phosphates , phosphorylated sugars , monophosphates, Chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Related URLs:
    Depositing user: Pure Administrator
    Date Deposited: 24 Oct 2011 13:37
    Last modified: 05 Sep 2014 12:44
    URI: http://strathprints.strath.ac.uk/id/eprint/35060

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