Reinvestigation of the synthesis of 1-deazauridine.
A thorough study for the synthesis of 1-deazauridine is described. 3-Bromo-2,6-dimethoxy-5-(beta-D-ribofuranosyl)pyridine, a synthetic precursor for 1-deazauridine, was prepared in seven steps from 2,6-dimethoxypyridine and d-ribose via the ribonolactone approach. Subsequent demethylation was unsuccessful but led to presumable anomerization and isomerization. The effort concluded that the synthesis of 1-deazauridine remained unachieved.
Jen
Cheng-Hung
CH
Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan.
Chien
Tun-Cheng
TC
D007783:Lactones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*; D012266:Ribose / Q000031:analogs & derivatives / Q000737:chemistry; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D007783:Lactones; D011725:Pyridines; C057020:ribonolactone; D012266:Ribose; D014529:Uridine