Tetrabutylammonium Fluoride → 2',3'-Didehydro-2',3'-dideoxyadenosine

Participants

Reaction Steps

To a solution of 16 (3.79 g, 10.92 mmol) in dry THF (40 mL), cooled in an ice-bath, was added 22 ml of a 1M solution of tetra-n-butylammonium flouride in THF (22 mL, 22.0 mmol). The mixture was stirred for 40 minutes at room temperature and concentrated. The resulting yellow syrupy residue was purified by chromatography on a silica gel column using a gradient of 3-5% methanol in CHCl3. Evaporation of the appropriate fractions yielded 2.21 g (86%) of 7: mp 184°-186° C. (methanol); 1H NMR (DMSO-d6) δ 3.59 (2H, dd, J=4.1 Hz, 5.27 Hz, 5'-H), 4.80-5.10 (2H, m, 4'-H and OH), 6.14 (1H, ddd, J=1.46 Hz, 1.76 Hz, 5.86 Hz, 2'-H), 6.47 (1H, ddd, J=1.46 Hz, 1.76 Hz, 5.87 Hz, 3'-H), 6.94 (1H, m, 1'-H), 7.25 (2H, br s, NH2), 8.157 (1H, s, 8-H), 8.167 (1H, s, 2-H).

Provenance & Evidence