Synthesis of 2,3’-Anhydro-2’-deoxyuridines and 2’,3’-Didehydro-2’,3’-dideoxyuridines Using Polymer Supported Fluoride
- 1 September 1995
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1995 (09) , 1121-1125
- https://doi.org/10.1055/s-1995-4070
Abstract
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.Keywords
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