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Synthesis of enantiomerically pure (S)-methanocarbaribo uracil nucleoside derivatives for use as antiviral agents and P2Y receptor ligands

  1. Author:
    Melman, A.
    Zhong, M.
    Marquez, V. E.
    Jacobson, K. A.

  2. Author Address

    Zhong, Minghong, Marquez, Victor E.] NCI, Med Chem Lab, Canc Res Ctr, NIH, Frederick, MD 21702 USA. [Melman, Artem] Clarkson Univ, Dept Chem & Biomol Sci, Potsdam, NY 13699 USA. [Melman, Artem, Jacobson, Kenneth A.] NIDDK, Mol Recognit Sect, Bioorgan Chem Lab, NIH, Bethesda, MD 20892 USA.
    1. Year: 2008
  2. Journal: Journal of Organic Chemistry
    1. 73
    2. 20
    3. Pages: 8085-8088
  4. Type of Article: Article
  1. Abstract:

    We have developed an approach toward enantiomerically pure (S)-methanocarba ribonucleosides based on several functional group transformations on a sensitive bicyclo[3.1.0]-hexane system. D-Ribose was transformed into methanocarba alcohol 3 followed by conversion of the OH group to a nitrile with inversion of configuration at C4. The nitrile group was subsequently reduced in two stages to the 5'-hydroxymethyl group. An ester group appended to a tertiary carbon (Cl) was transformed to an amino group as a nucleobase precursor.

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External Sources

  1. PMID: 18811198

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