Tetrahydrofuran → HCID 131724438, compound
Reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:54]=[CH:53][C:8]([C:9]([O:24][CH2:25][C@H:26]2[O:30][C@@H:29]([N:31]3[CH:39]=[C:37]([CH3:38])[C:35](=[O:36])[NH:34][C:32]3=[O:33])[CH2:28][C@:27]2([CH2:41][O:42]S(C2C=CC(C)=CC=2)(=O)=O)O)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10]2[CH:15]=[CH:14][C:13](OC)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1.C1C[O:58][CH2:57]C1>>[CH3:57][O:58][C:5]1([O:4][CH3:3])[CH:6]=[CH:7][C:8]([C:9]([O:24][CH2:25][C@H:26]2[O:30][C@@H:29]([N:31]3[CH:39]=[C:37]([CH3:38])[C:35](=[O:36])[NH:34][C:32]3=[O:33])[CH2:28][C@:27]32[CH2:41][O:42]3)([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:53][CH2:54]1Participants
4
Procedure
To a suspension of NaH (60% in mineral oil, 0.18 g; 7.5 mmol) in anhydrous THF (18 ml) at 0° C. under argon was added dropwise a solution of 5′-O-(4,4′-dimethoxytrityl)-3′-p-toluensulfonyloxymethylthymidine (1.5 g; 2.06 mmol) in THF (10 ml). The resulting reaction mixture was stirred at room temperature for 2 h, cooled to 0° C., and quenched by addition of water. The mixture was diluted with EtOAc (250 ml), washed with water (2×200 ml), then with 10% NaHCO3 (2×200 ml), dried over Na2SO4, and concentrated. The residue was purified by chromatography on silica (5% CH3OH in CH2Cl2) to yield 0.97 g (8.5%) of 5′-O-(4,4-dimethoxytrityl)-3′-C,O-methylene thymidine as a foam.
Workup
- customThe resulting reaction mixture
- temperaturecooled to 0° C.
- customquenched by addition of water
- additionThe mixture was diluted with EtOAc (250 ml)
- washwashed with water (2×200 ml)
- dry with materialwith 10% NaHCO3 (2×200 ml), dried over Na2SO4
- concentrationconcentrated
- customThe residue was purified by chromatography on silica (5% CH3OH in CH2Cl2)
Sources & evidence
- ORD record
- ord-e7be2c5652534b21a64fe4c2efcec969
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06743902B1
Reaction notes
Loading…