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Synthesis 1991; 1991(11): 1005-1008
DOI: 10.1055/s-1991-26631
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A More Expedient Approach to the Synthesis of Anti-HIV-Active 2,3-Dideoxy-2-fluoro-β-D-threo-pentofuranosyl Nucleosides

Ronald J. Wysocki, Jr.* , Maqbool A. Siddiqui, Joseph J. Barchi, Jr., John S. Driscoll, Victor E. Marquez
  • *Laboratory of Medicinal Chemistry, DTP, DCT, National Cancer Institute, NIH, Bethesda, MD 20892, USA
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Publikationsdatum:
29. April 2002 (online)

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Starting with 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose, a versatile method for the synthesis of 2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl nucleosides is described and illustrated with the synthesis of 9-(2, 3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine and 1-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)cytosine. In this approach, the deoxygenation of the 3′-OH function is performed at the sugar stage of the synthesis prior to coupling with the purine or pyrimidine base.