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Synthesis of a conformationally locked version of puromycin amino nucleoside

  1. Author:
    Choi, Y.
    George, C.
    Strazewski, P.
    Marquez, V. E.

  2. Author Address

    NCI, Med Chem Lab, Canc Res Ctr, Frederick, MD 21702 USA. NCI, Med Chem Lab, Canc Res Ctr, Frederick, MD 21702 USA. USN, Res Lab, Struct Matter Lab, Washington, DC 20375 USA. Univ Lyon 1, Lab Syntheses Biomol, F-69622 Villeurbanne, France. Marquez VE NCI, Med Chem Lab, Canc Res Ctr, Frederick, MD 21702 USA.
    1. Year: 2002
  2. Journal: Organic Letters
    1. 4
    2. 4
    3. Pages: 589-592
  4. Type of Article: Article
  1. Abstract:

    [GRAPHICS] A conformationally locked carbocyclic version of puromycin amino nucleoside was synthesized via Mitsunobu coupling of a 3-azido-substituted carbocyclic moiety with 6- chloropurine without interference from the azido group reacting with triphenylphosphine. The requisite 3-azido-substituted carbocyclic pseudosugar was prepared by a double inversion of configuration at C3' (nucleoside numbering) involving a nucleophilic displacement with azide.

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