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  • Accessing C-1 Phosphonylated 2-Acylamino Uronic Acids via 2-Nitro-glycals

    Author(s)
    Bhatt, Beenu
    Thomson, Robin J
    von Itzstein, Mark
    Griffith University Author(s)
    von Itzstein, Mark
    Thomson, Robin J.
    Bhatt, Beenu
    Year published
    2011
    Metadata
    Show full item record
    Abstract
    Two approaches are described for the synthesis of 2-acylamino uronic acid glycosyl phosphonates from readily accessible D-glucal. The first approach that entailed oxidation of the C-6 hydroxyl group followed by phosphonylation of the uronate 2-nitro-glycal, resulted in the formation of the ߭L-gulo-configured phosphonate. Reversing the reaction order resulted in the exclusive formation of the ߭D-gluco-configured phosphonate. In both cases the thermodynamic 1,2-trans-di-equatorial phosphonylation product is obtained.Two approaches are described for the synthesis of 2-acylamino uronic acid glycosyl phosphonates from readily accessible D-glucal. The first approach that entailed oxidation of the C-6 hydroxyl group followed by phosphonylation of the uronate 2-nitro-glycal, resulted in the formation of the ߭L-gulo-configured phosphonate. Reversing the reaction order resulted in the exclusive formation of the ߭D-gluco-configured phosphonate. In both cases the thermodynamic 1,2-trans-di-equatorial phosphonylation product is obtained.
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    Journal Title
    The Journal of Organic Chemistry
    Volume
    76
    Issue
    10
    DOI
    https://doi.org/10.1021/jo2002193
    Copyright Statement
    Self-archiving of the author-manuscript version is not yet supported by this journal. Please refer to the journal link for access to the definitive, published version or contact the author[s] for more information.
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Organic chemical synthesis
    Publication URI
    http://hdl.handle.net/10072/42790
    Collection
    • Journal articles

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