反应详情

4′-C-Aminomethyl-2′-deoxyuridine (13) (0.034 g, 0.13 mmol) was dissolved in anhydrous N,N-dimethylformamide (0.5 mL) at ambient temperature. Excess pentafluorophenyl acetate (0.88 g, 0.39 mmol) was then added directly to the reaction mixture as a solid. The resulting solution was stirred for 18 hours at ambient temperature. The solvent was then removed under vacuum and the residue re-dissolved in water and then washed with toluene. The aqueous layer was then separated and the solvent removed under vacuum. The title compound was obtained as an amorphous solid (0.032 g, 82%). δH(300 MHz, D2O) 7.68(1H, d, H-6), 6.11(1H, dd, H-1′), 5.71(1H, d, H-5), 4.44(1H, dd, H-3′), 4.49(2H, 2d, H-5′), 3.33(2H, 2d, 4′-C—CH2), 2.33(2H, m, H-2′), 1.89(3H, s, CH3CONH); δC(75.45 MHz, D2O) 175.60, 167.08, 152.43, 142.86, 102.93, 88.93, 85.57, 71.91, 63.16, 40.37, 39.15, 22.72; ES +ve m/z 300(M+H)+, 242(M−CH3CONH)+.

1. customThe solvent was then removed under vacuum
2. dissolutionthe residue re-dissolved in water
3. washwashed with toluene
4. customThe aqueous layer was then separated
5. customthe solvent removed under vacuum