Tetrabutylammonium Fluoride → N4-Acetyl-2',3'-didehydro-2',3'-dideoxycytidine

Participants

Reaction Steps

A solution of 32 (1.5 g, 4.1 mmol) in THF (30 ml) and 5 ml (5.0 mmol) of a 1M solution of tetra-n-butylammonium fluoride solution in THF were stirred in an ice-bath for 10 minutes and then at room temperature for 1 hour. The solvent was removed in vacuo. The resulting residue was purified by chromatography using 5% methanol in CHCl3 to obtain 0.88 g (85%) of 33 as colorless solid: mp 180°-182° C. dec (benzene-methanol); 1H NMR (DMSO-d6) 6 2.09 (3H, s, COCH3), 3.63 (2H, m, 5'-H), 4.85 (1H, m, 4'-H), 4.99 (1H, t, J=5.27 Hz, OH), 5.95 (1H, br d, J=5.8 Hz, 2'-H), 6.40 (1H, br d, J=5.8 Hz, 3'-H), 6.87 (1H, m, 1'-H), 7.15 (1H, d, J=7.3 Hz, 5-H), 8.20 (1H, d, J=7.3 Hz, 6-H), 10.86 (1H, s, NH).

Provenance & Evidence