Collect. Czech. Chem. Commun. 1996, 61, 1223-1232

Optically Active Furanoids Containing Cytosine-, Adenine- and Nicotinamide-Like Moieties

Ali Werfeli, Svatava Voltrová, Viktor Prutianov and Josef Kuthan

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic


3-Hydroxymethyl-5-(2,3-O-isopropylidene-β-D-erythro-furanosyl)-2-methylfuran (2) prepared from 3-ethoxycarbonyl derivative 1 was converted to 3-chloromethyl-5-(2,3-O-isopropylidene-β-D-erythro-furanosyl)-2-methylfuran (3). Compound 3 reacted with cytosine, adenine, 6-chloropurine, 6-mercaptopurine, and nicotinamide to corresponding optically active heterocyclic derivatives 5-10 and 14. The 6-chloro derivative 9 was converted to 6-alkoxy derivatives 11 and 12 by the reaction with methanol or ethanol, respectively, in the presence of diazabicyclooctane. Dithionite reduction of quaternary chloride 14 gave 1,4-dihydropyridine derivative 15 capable to transform ethyl phenylglyoxylate to optically active ethyl mandelate.

Keywords: 5-Deoxy-β-D-ribofuranose derivatives; NADH model reduction.