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Molecules 2001, 6(3), 203-207; doi:10.3390/60300203

Synthesis of 1-(2'-O-Methyl-ß-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical 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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Received: 12 October 2000 / Revised: 18 January 2001 / Accepted: 19 January 2001 / Published: 28 February 2001
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Abstract

Synthesis of the title compound,1-(2'-O-methyl-ß-D-ribofuranosyl)-1H-imidazo-[4,5-d]pyridazine-4,7(5H,6H)-dione (1), is reported. It was synthesized in four steps, starting from methyl 1-(ß-D-ribofuranosyl)imidazo-4,5-dicarboxylate (2). The 3',5'-hydroxyl groups of 2 was protected with a bis-silylating agent to form 3, which was then methylated to form the corresponding 2'-O-methyl derivative 5. The silyl deprotection of the latter (to form 6), followed by treatment with hydrazine afforded the target nucleoside 1. The reported nucleoside has potentially beneficial applications in biomedicine based on antisense and triple-helical nucleic acid technologies. View Full-Text
Keywords: Synthesis; Nucleoside Analogue; Imidazo[4; 5-d]pyridazine; 2'-O-Methyl Nucleoside Introduction Synthesis; Nucleoside Analogue; Imidazo[4; 5-d]pyridazine; 2'-O-Methyl Nucleoside Introduction
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Chen, H.-M.; Hosmane, R.S. Synthesis of 1-(2'-O-Methyl-ß-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications. Molecules 2001, 6, 203-207.

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