Acetone → 4-(2-Hexanon-1-yl)-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-pyrimidin-2-one

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Reaction Steps

A solution of 14a (0.77 g, 1.2 mmol) in 50 mL acetone is treated with a 0.1 M solution of Hg(OAc)2 (15 mL) in aqueous acetic-H2O (1:1) and the mixture stirred at room temperature for 18 hr. The reaction is further diluted with dichloromethane (100 mL), washed with cold saturated NaHCO3 solution, dried over magnesium sulfate and evaporated in vacuo. The resulting residue is flash-chromatographed using chloroform/acetone 19:1 to afford a yellowish solid. This solid is triturated with cold methanol to afford 15a, 0.47 g, 59%. 1H-NMR (DMSO-d6): 12.5 (s, 1H, enol); 8.0-7.4 (m, 16H, H-6 plus aromatic 6.15 (d, 1H, H-1′, J=2 Hz); 5.90 (m, 3H, H-5,2′,3′; 5.39 (s, 1H, vinylic, Jvinyl, allyl=<1 Hz)); 2.30, 1.47, 1.24 and 0.86 (4 m, 9H, n-butyl). Anal. Calcd for C36H34N2O8: C, 67.70; H, 5.37; N, 4.39. Found: C, 67.51; H, 5.28; N, 4.28.

Provenance & Evidence