1-(3,5-Di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-2-O-p-toluenesulphony-beta-D-ribofuranosyl)uracil → 1-(2-O-p-Toluenesulfonyl-4-C-(p-toluenesulfonyloxymethyl)-beta-D-ribofuranosyl)uracil

HRID 434286Notes

Reaction equation

HRID 434286 reaction equation
C([O:8][C@@H:9]1[C@@:13]([CH2:23][O:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)(=[O:27])=[O:26])([CH2:14][O:15]CC2C=CC=CC=2)[O:12][C@@H:11]([N:35]2[CH:42]=[CH:41][C:39](=[O:40])[NH:38][C:36]2=[O:37])[C@@H:10]1[O:43][S:44]([C:47]1[CH:52]=[CH:51][C:50]([CH3:53])=[CH:49][CH:48]=1)(=[O:46])=[O:45])C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[C:50]1([CH3:53])[CH:51]=[CH:52][C:47]([S:44]([O:43][C@@H:10]2[C@H:9]([OH:8])[C@@:13]([CH2:23][O:24][S:25]([C:28]3[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=3)(=[O:26])=[O:27])([CH2:14][OH:15])[O:12][C@H:11]2[N:35]2[CH:42]=[CH:41][C:39](=[O:40])[NH:38][C:36]2=[O:37])(=[O:46])=[O:45])=[CH:48][CH:49]=1

Participants

4

Reactant 1

HCID 106051711-(3,5-Di-O-benzyl-4-C-(p-toluenesulphonyloxymethyl)-2-O-p-toluenesulphony-beta-D-ribofuranosyl)uracil

Product 1

HCID 118013911-(2-O-p-Toluenesulfonyl-4-C-(p-toluenesulfonyloxymethyl)-beta-D-ribofuranosyl)uracilYield 51.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound 75 (0.80 g, 1.0 mmol) in absolute ethanol (2 cm3) was added 20% palladium hydroxide over carbon (0.80 g) and the mixture was degassed several times with hydrogen and stirring was continued under hydrogen for 48 h. The catalyst was filtered off and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane/methanol (99:1, v/v) as eluent to give nucleoside 76A (0.30 g, 49%) as a white solid material. δH (CD3OD) 7.67 (4H, m), 7.45 (1H, d, J 8.2 Hz), 7.34 (4H, m), 5.86 (1H, d, J 8.0 Hz), 5.40 (1H, d, J 8.1Hz), 4.95 (1H, m), 4.35 (1H, d, J 5.0 Hz), 4.17 (2H, m), 3.61 (2H, s), 2.40 (6H, s). δc (CD3OD) 165.4, 151.6, 147.5, 146.6, 141.3, 134.0, 133.8, 131.4, 130.9, 129.2, 128.9, 103.7, 88.0, 85.4, 80.7, 72.4, 71.0, 64.3, 21.7, 21.6. FAB-MS m/z 583 [M+H]+.

Workup

  1. customthe mixture was degassed several times with hydrogen
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a6237f23b2c04318b171b44821141e58
Source dataset
uspto-grants-2003_12
Patent number
US06670461B1

Reaction notes

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