Synthesis, conformation analysis and biological evaluation of 2-(2,3-dideoxy-beta-D-ribofuranosyl)pyridine-4-carboxamide

2-(2,3-Dideoxy-beta-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. alpha/beta-Separation was done by semi preparative hplc on a Lichrosorb 10 RP 8 column. In addition 2D-NOESY nmr spectroscopy was used for the assignment of the alpha/beta-anomers of (2). High resolution H-1 nmr allowed us to do a conformation analysis of compound (beta-2). Finally the beta-anomer of (2) was evaluated for its biological activity.