HCID 11487746, compound → HCID 11425688, compound

Participants

Reaction Steps

To a stirred solution of nucleoside 28 (180 mg, 0.40 mmol) in ethanol (3 cm3) was added 10% palladium hydroxide over carbon (90 mg). The mixture was degassed several times with argon and placed under a hydrogen atmosphere. The reaction mixture was stirred at room temperature for 6 h, then filtered through celite. The filtrate was evaporated under reduced pressure and the residue was purified by silica gel column chromatography using dichloromethane/methanol (96:4, v/v) as eluent to give nucleoside 29 as a white solid material (92 mg, 86%). δH (CD3OD) 7.79 (1H, d, J 1.2, 6-H), 5.91 (1H, d, J 2.5, 1′-H), 4.96 (1H, d, J 2.5, 2′-H), 4.92 (1H, d, J 7.4, 1″-Ha), 4.58 (1H, dd, J 0.9, 7.4, 1″-Hb), 3.98 (1H, dd, J 7.3, 12.8, 5′-Ha), 3.87-3.82 (2H, m, 4′-H, 5′-Hb), 3.34 (2H, s, 3′-OH, 5′-OH), 1.87 (3H, d, J 1.3, CH3). δC (CD3OD) 166.5 (C-4), 152.1 (C-2), 140.1 (C-6), 110.1 (C-5), 91.2 (C-2′), 85.1 (C-1′), 84.0 (C-4′), 79.6 (C-3′), 78.6 (C-1″), 61.1 (C-5′), 12.3 (CH3).

Provenance & Evidence