7-Deazainosine Derivatives: Synthesis and Characterization of 7- and 7,8-Substituted Pyrrolo [2,3-d]Pyrimidine Ribonucleosides

Abstract

The synthesis of model 7 deazapurine derivatives related to tubercidin and toyocamycin has been performed. Tubercidin derivatives were obtained by simple conversion of the amino group of the heterocyclic moiety of the starting 7-deazadenosine compounds, into a hydroxyl group. Preparation of toyocamycin derivatives was accomplished by treatment of the silylated 6-bromo-5-cyanopyrrolo[2,3-d]pyrimidin-4-one with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose. The glycosylation reaction afforded a mixture of 8-bromo 7-cyano 2′,3′,5′ tri-O-benzoyl 7-deazainosine and 6-bromo-5-cyano-3-(2′,3′,5′-tri-O-benzoyl-β-d-ribofuranosyl)pyrrolo[2,3-d]-pyrimidin-4-one isomers: The structures were assigned on the basis of NMR spectroscopy studies. Next deprotection treatment gave the novel 7-deazainosine ribonucleosides.