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Synthesis 1995; 1995(9): 1121-1125
DOI: 10.1055/s-1995-4070
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Synthesis of 2,3’-Anhydro-2’-deoxyuridines and 2’,3’-Didehydro-2’,3’-dideoxyuridines Using Polymer Supported Fluoride

Erik Larsen, Thomas Kofoed, Erik B. Pedersen*
  • *Department of Chemistry, Odense University, Campusvej 55, DK-5230 Odense M, Denmark, Fax +45(66)158780
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Publication Date:
31 December 2000 (online)

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Reaction of methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-α,β-D-erythro-pentofuranoside (2) with silylated uracils 3 using trimethylsilyl trifluoromethanesulfonate (TMS triflate) as catalyst afforded after crystallization in Et2O the corresponding β-nucleosides 4. Reaction of 4 with tetrabutylammonium fluoride (TBAF) or Amberlyst A-26 resin (F--form) in THF at room temperature or at reflux gave the corresponding deprotected 2,3’-anhydro-2’-deoxyuridines 6 and 2’,3’-didehydro-2’,3’-dideoxyuridines 7, respectively.

polymer supported fluoride - 2,3’-anhydro-2’-doxyuridines - 2’,3’-didehydro-2’,3’-dideoxyuridine