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Open AccessArticle

Synthesis of 1-(2'-Deoxy-ß-D-ribofuranosyl)-1H-imidazo[4,5-d]-pyridazine-4,7(5H,6H)-dione: A Potential Building Block for Antisense Applications

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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Molecules 2000, 5(12), 1187-1193; https://doi.org/10.3390/51201187
Received: 28 August 2000 / Revised: 10 October 2000 / Accepted: 11 October 2000 / Published: 15 December 2000
Synthesis of the title compound,1-(2'-deoxy-b-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione (1), is reported. It was synthesized in five steps, commencing with methyl 1-(b-D-ribofuranosyl)imidazo-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. View Full-Text
Keywords: Synthesis; Nucleoside Analogue; Imidazo[4; 5-d]pyridazine; 2'-Deoxy Nucleoside Analogue Synthesis; Nucleoside Analogue; Imidazo[4; 5-d]pyridazine; 2'-Deoxy Nucleoside Analogue
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Chen, H.-M.; Hosmane, R.S. Synthesis of 1-(2'-Deoxy-ß-D-ribofuranosyl)-1H-imidazo[4,5-d]-pyridazine-4,7(5H,6H)-dione: A Potential Building Block for Antisense Applications. Molecules 2000, 5, 1187-1193.

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