Reaction Steps
To a solution of compound 42 (55 mg, 0.09 mmol) in THF (10 mL), n-Bu4NF (63 mg, 0.20 mmol) was added. The mixture was stirred at room temperature for four hours and concentrated in vacuo, and the residue was purified by silica gel column chromatography to yield 5-(2-nitrobenzyloxy)methyl-2′-deoxycytidine 43 (34 mg, 96%). 1H NMR (400 MHz, DMSO-d6): δ 8.05 (d, J=8.0 Hz, 1H, Ph-H), 7.89 (s, 1H, H-6), 7.74 (m, 2H, Ph-H), 7.55 (m, 1H, Ph-H), 7.39 (br s, 1H, D2O exchangeable, NH2), 6.74 (br s, 1H, D2O exchangeable, NH2), 6.12 (t, 1H, J=6.4 Hz, H-1′), 5.21 (br s, 1H, D2O exchangeable, 3′-OH), 4.99 (br s, 1H, D2O exchangeable, 5′-OH), 4.81 (s, 2H, Ph-CH2), 4.30 (dd, 2H, J=11.6 Hz, 5-CH2), 4.20 (m, 1H, H-3′), 3.76 (m, 1H, H-4′), 3.55 (m, 2H, H-5′), 2.11 (m, 1H, H-2′a), 1.95 (m, 1H, H-2′b).
