Methane → HCID 10663046, compound

Participants

Reaction Steps

To a solution of nucleoside 16 (1.20 g, 2.43 mmol) in methanol (10 cm3) was added 20% palladium hydroxide over charcoal (250 mg) and the mixture was carefully degassed under reduced pressure. An atmosphere of hydrogen was applied and stirring was continued for 12 h. The catalyst was removed by filtration of the reaction mixture through a glass column (1×8 cm) packed with silica gel in methanol. The column was additionally washed with methanol (20 cm3). All fractions were collected, evaporated to dryness and co-evaporated with petroleum ether to yield a glass-like solid. This residue was purified by silica gel chromatography eluting with a gradient of 5-10% methanol in dichloromethane (v/v). The fractions containing the product were collected, combined and evaporated to dryness. The residue was dissolved in anhydrous methanol (5 cm3) and anhydrous benzene (100 cm3) was added. Lyophilisation yielded nucleoside 17 (0.61 g, 79%) as a white solid material. δH (CD3OD) 7.45 (1H, s, 6-H), 5.93 (1H, s, 1′-H), 4.15-3.81 (5H, m, 5′-Ha, 5′-Hb, 2″-Ha, 2″-Hb, 4′-H), 3.43 (3H, s, CH3—O), 2.47-2.40 (1H, m, 1″-Ha), 2.03-1.93 (1H, m, 1″-Hb), 1.92 (3H, s, CH3). δC (CD3OD) 164.1 (C-4), 150.1 (C-2), 138.3 (C-6), 109.6 (C-5), 108.3 (C-2′), 84.4, 84.1, 82.4 (C-1′, C-3′, C-4′), 68.0, 59.5 (C-5′, C-2″), 49.6 (CH3—O), 34.0 (C-1″), 10.5 (CH3). FAB-MS m/z 315.13 [M+H]+, 337.09 [M+Na]+ (Found: C, 49.9; H, 5.7; N, 8.2; C13H18O7N2 requires C, 49.7; H, 5.8; N, 8.9%).

Provenance & Evidence