Nucleosides XI. Synthesis and Antiviral Evaluation of 5′-Alkylthio-5′-deoxy Quinazolinone Nucleoside Derivatives as S-Adenosyl-L-homocysteine Analogs

Abstract

4-Amino-1-(β-D-ribofuranosyl)quinazolin-2-one (3) was prepared by a direct glycosylation of 4-aminoquinazolin-2-one (7) using the Vorbruggen's silylation method and provided exclusively the β-anomer. This quinazoline nucleoside and its 2′,3′-O-isopropylidene derivative (9) did not undergo the coupling reaction with dialkyl disulfides in the presence of tri-n-butylphosphine unless their 4-amino groups were protected by N,N-dimethylaminomethylidene. This approach provides a viable alternative synthetic route to 5′-alkylthio-5′-deoxy nucleosides.