ACYCLIC NUCLEOSIDES - SYNTHESIS OF 1-[(1-HYDROXY-2-PROPOXY) METHYL]THYMINE, 6-AZATHYMINE, URACIL, AND 6-AZAURACIL AS POTENTIAL ANTIVIRAL AGENTS

A series of acyclic nucleosides have been synthesized. Thymine, 6-azat hymine, uracil, and 6-azauracil were silylated with hexamethyldisilaza ne in the presence of ammonium sulfate and then coupled with 1-benzylo xy-2-chloromethoxypropane to give the corresponding 1-(1-benzyloxy-2-p ropoxy)methyl derivatives. A minor quantity of benzyloxymethylated pro duct was also obtained in each case. Hydrogenolysis of the protected a cyclic nucleosides with palladium(II) hydroxide afforded the title com pounds. None of the compounds exhibited significant antiviral activity against human immunodeficiency virus (HIV).