ABSTRACT
Moeller first reported the use of 4'-deoxypyridoxine, which he obtained from E. Merck & Co. However, the synthesis appears to be that of Harris who prepared 4'-deoxypyridoxine by hydrogenating pyridoxine or 4'-ethoxypyridoxine in alcohol. 4'- and 5'-deoxypyridoxines have been identified as impurities in pyridoxine labeled with tritium and carbon-14. Argoudelis and Kummerow felt the specific activity of the impurities was probably much higher than that of the pyridoxine itself. The ethylchloroformate reaction is not specific for the phenol group in pyridoxine or other compounds with a hydroxymethyl group in the 4-position because the acyl group will migrate from the 3- to the 4'-position. Doktorova et al. reported the synthesis of 5-deoxypyridoxal by manganese dioxide oxidation of 5'-deoxypyridoxine. Mulligan and Snell used the manganese dioxide procedure to convert labeled 5'-deoxypyridoxine to labeled 5'-deoxypyridoxal. The 5'-deoxypyridoxal and unreacted 5'-deoxypyridoxine were purified by chromatography on silica gel and Pll phospho-cellulose.
