Synthesis of 1-2-Deoxy-ß-D-ribofuranosyl-1H-imidazo4,5-d-pyridazine-4,75H,6H-dione: A Potential Building Block for Antisense ApplicationsReportar como inadecuado




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Laboratory for Drug Design and Synthesis, Department of Chemistry & Biochemistry, University of Maryland, Baltimore County UMBC, 1000 Hilltop Circle, Baltimore, Maryland 21250, USA





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Abstract Synthesis of the title compound,1-2-deoxy-b-D-ribofuranosyl-1H-imidazo4,5-dpyridazine-4,75H,6H-dione 1, is reported. It was synthesized in five steps, commencing with methyl 1-b-D-ribofuranosylimidazo-4,5-dicarboxylate 2. The 3,5-hydroxyl groups of 2 were protected with a bis-silylating agent to form 3, which was then converted into the corresponding 2-thionocarbonate derivative 5. The reduction of the latter with tri-n-butyltin hydride to form 6, followed by silyl deprotection with tetra-nbutylammonium fluoride, afforded 7. Treatment of the latter with hydrazine hydrate yielded the target nucleoside 1.

Keywords: Synthesis; Nucleoside Analogue; Imidazo4; 5-dpyridazine; 2-Deoxy Nucleoside Analogue Synthesis; Nucleoside Analogue; Imidazo4; 5-dpyridazine; 2-Deoxy Nucleoside Analogue





Autor: Huan-Ming Chen and Ramachandra S. Hosmane *

Fuente: http://mdpi.com/



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