Nucleosides and Nucleotides p. 1201 - 1213 (1994)
Update date:2022-08-04
Topics: Synthesis Acyclic nucleosides Uracil 6-azauracil Antiviral agents
Wang
Chen
Tzeng
A series of acyclic nucleosides have been synthesized. Thymine, 6- azathymine, uracil, and 6-azauracil were silylated with hexamethyldisilazane in the presence of ammonium sulfate and then coupled with 1-benzyloxy-2- chloromethoxypropane to give the corresponding 1-(1-benzyloxy-2- propoxy)methyl derivatives. A minor quantity of benzyloxymethylated product was also obtained in each case. Hydrogenolysis of the protected acyclic nucleosides with palladium(II) hydroxide afforded the title compounds. None of the compounds exhibited significant antiviral activity against human immunodeficiency virus (HIV).
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Doi:10.1021/acs.orglett.8b03078
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