HCID 11487746, compound → HCID 11425688, compound

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, J7.4, 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).

1. customThe mixture was degassed several times with argon
2. filtrationfiltered through celite
3. customThe filtrate was evaporated under reduced pressure
4. customthe residue was purified by silica gel column chromatography

ORD record

ord-4cfda7c5ec33420b9f3735a4f344b0cf

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08153365B2