Nucleosides, XLIII1) Synthesis and Properties of 04-Alkylthymidines

Abstract Various 04-alkylthymidines 14–20 have been synthesized by two different methods. 04-Alkylation takes place with 3′,5′-di-0-acetyl- (2) and 3′,5′-di-0-benzoylthymidine (3) respectively in a silver ion catalysed reaction with alkyl halides, whereas the azolide approach makes use of a nucleophilic displacement of the appropriate intermediate by alkoxides and subsequent deacylation to the free nucleosides. Structural proofs are based on elemental analyses, UV- and 1H-NMR-spectra.