Synthesis of 2,3'-anhydro-2'-deoxyuridines and 2,3'-didehydro-2',3'-dideoxyuridines using polymer supported fluoride

Article abstract of DOI:10.1055/s-1995-4070

Reaction of methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-α,β-D-eryt hro-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.