Utility Of 1-(5'-Acetoxy-4'-Benzoyltetrahydrofuran-2'-Yl)-3-Benzyloxymethylthymine For The Synthesis Of 5'-Modified Furanoid Nucleoside Analogs

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 beta-glycosylation products.