Download PDF
Synlett 1996; 1996(4): 346-348
DOI: 10.1055/s-1996-5428
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

 PDF Download  Permissions and Reprints All articles of this category

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