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Synthesis of Enantiomerically Pure (S)-Methano-carba-ribo Uracil Nucleoside Derivatives for Use as Antiviral Agents and P2Y Receptor Ligands.

  作者 Melman, Artem;Zhong, Minghong;Marquez, Victor E.;Jacobson, Kenneth A.;  
  选自 期刊  Journal of Organic Chemistry;  卷期  2008年73-20;  页码  8085-8088  
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[摘要]We have developed an approach toward enantiomerically pure (S)-methano-carba ribonucleosides based on several functional group transformations on a sensitive bicyclo[3.1.0]hexane system. D-Ribose was transformed into methanocarba alc. 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 (C1) was transformed to an amino group as a nucleobase precursor.

 
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