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

Authors :
Nunzia Ciliberti
Elisa Durini
Silvia Vertuani
Stefano Manfredini
Source :
ChemInform. 39
Publication Year :
2008
Publisher :
Wiley, 2008.

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.

Details

ISSN :
15222667 and 09317597
Volume :
39
Database :
OpenAIRE
Journal :
ChemInform
Accession number :
edsair.doi...........c9c31ab691f9345087bd1402c989248f
Full Text :
https://doi.org/10.1002/chin.200843197