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Paper | Regular issue | Vol 43, No. 2, 1996, pp.287-304
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7207
Synthesis, Conformation Analysis and Biological Evaluation of 2-(2,3-Dideoxy-β-D-ribofuranosyl)pyridine-4-carboxamide

Pieter E. Joos,* Eddy L. Esmans, Frank C. Alderweireldt, André De Bruyn, Jan Balzarini, and Erik De Clercq

*University of Antwerp (RUCA), Department of Chemistry, Groenenborgerlaan 171, B-2020-Antwerp, Belgium

Abstract

2-(2,3-Dideoxy-β-D-ribofuranosyl)pyridine-4-carboxamide (2) was synthesized starting from the protected sugar analogue (3). Coupling of this compound with 2-lithio-4-(4,5-dihydro-4,4-dimethyloxazol-2-yl)pyridine (4), subsequent mesylation, reduction, deprotection and ammonolysis gave (2) as an anomeric mixture. α/β-Separation was done by semi preparative hplc on a Lichrosorb 10 RP 8 colum. In addition 2D-NOESY nmr spectroscopy was used for the assignment of the α/β-anomers of (2). High resolution 1H nmr allowed us to do a conformation analysis of compound (β-2). Finally the β-anomer of (2) was evaluated for its biological activity.