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Stereospecific synthesis of a novel series of pyridine nucleosides
Authors:Eddy J Freyne  Eddy L Esmans  Josef A Lepoivre  Frank C Alderweireldt
Institution:University of Antwerp (RUCA), Laboratory of Organic Chemistry, Groenenborgerlaan, 171, B 2020 Antwerp Belgium
Abstract: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° gave the corresponding 1-(3,5-di-O-benzoyl-β-d-ribofuranosyl))-3,5-disubstituted pyridinium chlorides in excellent yield (90%). 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.
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