Tetrahydrofuran → HCID 15405113, 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]OS(C2C=CC(C)=CC=2)(=O)=O)[OH:40])([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:13]1[CH:12]=[CH:11][C:10]([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:40]3)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8]2[CH:53]=[CH:54][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)=[CH:15][CH:14]=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 (85%) 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-ea8ba168bc9a4a299cf078092331c6aa
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05712378
Reaction notes
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