Synthesis Of Brivudin, An Antivirus Agent In Nucleoside

Some of antiviral agents in nucleoside were briefly described in this thesis. Brivudin, a highly potent and selective inhibitor of herpes simplex virus type 1 (HSV-1) and varicella-zoster virus (VZV) infections was imported into China since 1995. Its acting mechanism and antiviral activity spectrum was also introduced in this thesis.Starting from uracil and 2-deoxy-D-ribose, Brivudin was synthesized via an 11-step sequence such as 5-iodination, Heck reaction, hydrolysis and condensatioa The total yield reached up to 7.2 %. The structure of the target molecule was determined by ¹H NMR, ¹³C NMR, IR and ESI-MS.The synthetic route of Brivudin was carefully examined and some of the procedures were improved. In the case of preparing compound 27 via Heck reaction, the type and amount of the catalysts, temperature, and solvent effects were extensively examined It was found that catalyst containing Pd(OAc)₂ or PdCl₂ showed nearly the same activity, and 5.0 mol % of catalyst could carry the reaction in perfect yield, and the solvent was replaced from dioxane to acetonitrile.