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Synthesis of 1-(2'-O-Methyl-ß -D-Ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dion: an Attractive Building Block for Antisense and Triple-helical Applications
Published:
11 September 2000
by MDPI
in The 4th International Electronic Conference on Synthetic Organic Chemistry
session Bioorganic Chemistry and Natural Products
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.
Keywords: Synthesis, Nucleoside Analogue, Imidazo[4,5-d]pyridazine, 2'-O-Methyl Nucleoside