Tubercidin

Its Conversion to 2', 3'-Didehydro-2', 3'-dideoxy Derivatives

Abstract

Treatment of N⁶, N⁶, 5'-O-tribenzoyl-2', 3'-O-isopropylidenetubercidin (VI) with aqueous acetic acid afforded N⁶, 5'-O-dibenzoyltubercidin (V), which was mesylated to yield the dimesylate X. On treatment of X with sodium iodide and zinc dust, the 2', 3'-unsaturated derivatives of tubercidin XI and XIII were obtained.
N⁶, 5'-O-Dibenzoyltubercidin 2', 3'-thionocarbonate (XIV), prepared from V by treatment with Corey-Winter reagent, was converted to the 1-methyl-2', 3'-unsaturated derivative XV in refluxing trimethyl phosphite.