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Synthesis 1994; 1994(11): 1163-1166
DOI: 10.1055/s-1994-25664
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Efficient and Stereoselective Synthesis of 3′-Deoxy 3′ -C-Branched-Chain Substituted Thymidine

Yogesh S. Sanghvi* , Ramesh Bharadwaj, Françoise Debart, Alain De Mesmaeker
  • *Isis Pharmaceuticals, 2292 Faraday Avenue, Carlsbad, California 92008, USA
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Publication Date:
25 April 2002 (online)

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In this report, we provide for the first time a facile, efficient, and stereoselective synthesis of 1-[5-O-(tert-butyldiphenylsilyl)-2, 3-dideoxy-3-C-formyl-β-D-erythro-pentofuranosyl] thymine (12), using an intermolecular radical C-C bond formation reaction. The utility of this compound for antisense application is discussed and, as an extension, 12 was converted into 1-[2,3-dideoxy-3 -C-(hydroxymethyl)-β-D-erythro-pentofuranosyl]thymine (14), a potent antiviral and antitumor agent.