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Chemical conversion of uridine to 8,5′‐ O ‐cyclo‐3‐deazaguanosine
Author(s) -
Tanaka Hiromichi,
Veda Tohru
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160247
Subject(s) - chemistry , derivative (finance) , hydroxymethyl , cyanide , uridine , ammonia , nucleoside , imidazole , formaldehyde , carboxylic acid , medicinal chemistry , organic chemistry , stereochemistry , rna , economics , gene , biochemistry , financial economics
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.