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Molecules 2000, 5(12), 1187-1193; doi:10.3390/51201187
Article

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

 and *
Laboratory for Drug Design and Synthesis, Department of Chemistry & Biochemistry, University of Maryland, Baltimore County (UMBC), 1000 Hilltop Circle, Baltimore, Maryland 21250, USA
* Author to whom correspondence should be addressed.
Received: 28 August 2000 / Revised: 10 October 2000 / Accepted: 11 October 2000 / Published: 15 December 2000
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Abstract

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.
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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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