HCID 15405113, compound → HCID 15405114, compound
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:47]=[CH:46][C:12]([C:13]([O:28][CH2:29][C@H:30]2[O:34][C@@H:33]([N:35]3[CH:43]=[C:41]([CH3:42])[C:39](=[O:40])[NH:38][C:36]3=[O:37])[CH2:32][C@:31]32[CH2:45][O:44]3)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1>C1COCC1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([O:28][CH2:29][C@H:30]2[O:34][C@@H:33]([N:35]3[CH:43]=[C:41]([CH3:42])[C:39](=[O:40])[NH:38][C:36]3=[O:37])[CH2:32][C@:31]2([CH3:45])[OH:44])([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:12]2[CH:46]=[CH:47][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)=[CH:15][CH:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred, suspension of lithium aluminum hydride (58 mg; 1.53 mmol) in anhydrous THF (10 ml) at 0° C. under argon was added dropwise a solution of 5′-O-(4,4′-dimethoxytrityl)-3′-C,O-methylenethymidine (385 mg; 0.692 mmol) in THF (10 ml). The reaction mixture was stirred at 0° C. for 1 h and the reaction quenched by slow addition of 10% NaHCO3, The resulting mixture was diluted with EtOAc (30 ml), washed with NaHCO3 (3×20 ml, dried over Na2SO4, and concentrated. The residue was purified by chromatography on silica (5% CH3OH in CHCl3) to yield 306 mg (79%) of 5′-O-(4,4′-dimethoxytrityl)-3′-C-methylthymidine as a foam.
Workup
- customthe reaction quenched by slow addition of 10% NaHCO3
- additionThe resulting mixture was diluted with EtOAc (30 ml)
- washwashed with NaHCO3 (3×20 ml
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe residue was purified by chromatography on silica (5% CH3OH in CHCl3)
Sources & evidence
- ORD record
- ord-47f1169e651643bab0735cac8ed7d3dc
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06743902B1
Reaction notes
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