Chemical conversion of uridine to 8,5′-O-cyclo-3-deazaguanosine |
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Authors: | Hiromichi Tanaka Tohru Veda |
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Abstract: | Treatment of 1-(2,3-O-isopropy lidene-β-D-ribofuranosyl)-2-oxo-4-imidazoline-4-carboxylic acid methyl ester with formaldehyde gave the 5-hydroxymethyl derivative which, after aeetylalion, gave the 5-eyanomelhyl derivative by treatment with tetra-n-butylammonium cyanide. The 2,5′-O-cyclo derivative of the 5-cyanomethylimidazole-4-carboxylate was converted to the title compound by treatment with ammonia. The present sequence of reactions furnished the chemical conversion of uridine to a 3-deazaguanosine via the imidazole nucleoside as the intermediate. |
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