HCID 57310848, compound → HCID 15546052, compound

HRID 659853Notes

Reaction equation

HRID 659853 reaction equation
C([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@:10]1([CH2:24][O:25]CC1C=CC=CC=1)[O:11][C@H:12]2[N:16]1[CH:23]=[CH:22][C:20](=[O:21])[NH:19][C:17]1=[O:18])C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[OH:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@:10]1([CH2:24][OH:25])[O:11][C@H:12]2[N:16]1[CH:23]=[CH:22][C:20](=[O:21])[NH:19][C:17]1=[O:18]

Participants

4

Reactant 1

HCID 57310848HCID 57310848, compound

Product 1

HCID 15546052HCID 15546052, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound 43 (0.35 g, 0.8 mmol) in absolute ethanol (2 cm3) was added 20% palladium hydroxide over carbon (0.37 g) and the mixture was degassed several times with hydrogen and stirred under the atmosphere of hydrogen for 4 h. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using dichloramethane/methanol (9:1, v/v) as eluent to give nucleoside 44 as a white solid material (0.16 g, 78%). δH (CD3OD) 7.88 (1H, d, J 8.1, 6-H), 5.69 (1H, d, J 8.1, 5-H), 5.55 (1H, s, 1′-H), 4.28 (1H, s, 2′-H), 4.04 (1H, s, 3′-H), 3.96 (1H, d, J 7.9, 1″-Ha), 3.91 (2H, s, 5′-H), 3.76 (1H, d, J 7.9, 1″-Hb). δC (CD3OD) 172.95 (C-4), 151.82 (C-2), 141.17 (C-6), 101.97 (C-5), 90.52, 88.50 (C-1′, C-4′), 80.88, 72.51, 70.50, 57.77 (C-2′, C-3′, C-5′, C-1″). FAB-MS m/z 257 [M+H]+.

Workup

  1. customthe mixture was degassed several times with hydrogen
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-57215428634f4cd0ab688ea377b34cea
Source dataset
uspto-grants-2011_12
Patent number
US08080644B2

Reaction notes

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