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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.
    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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