HCID 136348252, compound → HCID 136347718, compound

HRID 1797364Notes

Reaction equation

HRID 1797364 reaction equation
C([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@:10]1([CH2:32][O:33]CC1C=CC=CC=1)[O:11][C@H:12]2[N:16]1[CH:24]=[N:23][C:22]2[C:21](=[O:25])[NH:20][C:19]([NH:26][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])=[N:18][C:17]1=2)C1C=CC=CC=1>CO.[Pd]>[OH:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@:10]1([CH2:32][OH:33])[O:11][C@H:12]2[N:16]1[CH:24]=[N:23][C:22]2[C:21](=[O:25])[NH:20][C:19]([NH:26][C:27](=[O:31])[CH:28]([CH3:29])[CH3:30])=[N:18][C:17]1=2

Participants

4

Reactant 1

HCID 136348252HCID 136348252, compound

Product 1

HCID 136347718HCID 136347718, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of nucleoside 50 (717 mg, 1.31 mmol) and 10% palladium over carbon (500 mg) was suspended in methanol (8 cm3) at room temperature. The mixture was degassed several times under reduced pressure and placed under a hydrogen atmosphere. After stirring for 24 h the mixture was purified by silica gel column chromatography using methanol/dichloromethane (8-20%, v/v) as eluent to give nucleoside 51 as a glass-liked solid (440 mg, 92%). δH (CD3OD) 8.12 (1H, br s, 8-H), 5.86 (1H, s, 1′-H), 4.50 (1H, s, 2′-H), 4.30 (1H, s, 3′-H), 4.05 (1H, d, J 8.0, 1″-Ha), 3.95 (2H, s, 5′-H), 3.87 (1H, d, J 7.9, 1″-Hb), 2.74 (1H, m, CHCO), 1.23 (6H, d, J 6.9, CH3CH). δC (CD3OD, signals from the carbohydrate part) 90.2, 87.6 (C-1′, C-4′), 81.1 (C-3′), 72.9 71.3 (C-2′, C-5′), 58.2 (C-1″), 37.1 (COCH), 19.5 (CH3CH). FAB-MS m/z 366 [M+H]+.

Workup

  1. customThe mixture was degassed several times under reduced pressure
  2. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e1914dea5b1c4c6fa5de8083554c6091
Source dataset
uspto-grants-2006_04
Patent number
US07034133B2

Reaction notes

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