STEREOSPECIFIC SYNTHESIS OF A NOVEL SERIES OF PYRIDINE NUCLEOSIDES

Article abstract of DOI:10.1016/0008-6215(80)90003-8

Condensation of 3,5-di-O-benzoyl-β-D-ribofuranosyl chloride severally with 3-acetyl-5-alkylpyridines, 5-alkyl-3-methoxycarbonylpyridines (alkyl= Me, Et, Pr, and iPr), 5-isopropylnicotinamide, and 3,5-diacetylpyridine bis(ethylene acetal) in acetonitrile at -5 deg C gave the corresponding 1-(3,5-di-O-benzoyl-β-D-ribofuranosyl)-3,5-disubstituted pyridinium chlorides in excellent yield (90percent).From the reaction of a series of 2,3-O-isopropylidene-β-D-ribofuranosyl halides with 3-acetyl-5-methyl-pyridine at room temperature, the α-nucleosides were obtained.