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Synlett 1996; 1996(4): 346-348
DOI: 10.1055/s-1996-5428
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Utility of 1-(5’-Acetoxy-4’-Benzoyltetrahydrofuran-2’-yl)-3-Benzyloxymethylthymine for the Synthesis of 5’-Modified Furanoid Nucleoside Analogs1

Kelly Teng* , Ramesh Bharadwaj, P. Dan Cook
  • *Department of Medicinal Chemistry, Isis Pharmaceuticals, 2292 Faraday Avenue, Carlsbad, California, 92008
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Publication History

Publication Date:
31 December 2000 (online)

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A series of 5’-modified furanoid nucleosides have been prepared in very good yields by the reaction of 1-(5’-acetoxy-4’-benzoxytetrahydrofuran-2’-yl)-3-benzyloxymethylthymine (1) with alcohols, a sulfide, and TMS-azide in the presence of TMSOTf. The reactions proceed in a stereospecific manner to provide only β-glycosylation products.

Vorbrüggen-type reaction - TMSOTf - 5’-modified furanoid nucleosides