4-Substituted nicotinic acids and nicotinamides. Part III. Preparation of 4-methylnicotinic acid riboside

Abstract

A method for the synthesis of nicotinic acid ribosides is described. The stepwise reaction between the tetra-n-butylammonium salt of nicotinic acid and 3,5-di-O-benzoyl-β-D-ribofuranosyl chloride gives 1-O-nicotinoyl-3,5-di-O-benzoyl-D-ribofuranose and 1-(3,5-di-O-benzoyl-D-ribofuranosyl)-3-(3,5-di-O-benzoyl-D-ribofuranosyloxycarbonyl)pyridinium chloride. The riboside obtained by stepwise hydrolysis of the quaternary derivative was essentially the β-anomer. 4-Methylnicotinic acid derivatives were similarly obtained.