反応式
CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[CH3:15][O:16][C:17](=[O:59])[CH2:18][O:19][CH2:20][C:21]#[C:22][CH2:23][C@H:24]1[C:28](=[O:29])[CH2:27][C@@H:26]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[C@@H:25]1[C:38]1[CH:43]=[CH:42][C:41]([CH:44]([O:51][Si:52]([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:54])[CH3:53])[CH:45]2[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]2)=[CH:40][CH:39]=1.OO.[NH4+].[Cl-]>C1COCC1>[CH3:15][O:16][C:17](=[O:59])[CH2:18][O:19][CH2:20][C:21]#[C:22][CH2:23][C@H:24]1[C@@H:28]([OH:29])[CH2:27][C@@H:26]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[C@@H:25]1[C:38]1[CH:39]=[CH:40][C:41]([CH:44]([O:51][Si:52]([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:54])[CH3:53])[CH:45]2[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]2)=[CH:42][CH:43]=1参加物
6
反応物 4
生成物 1
試薬・触媒・溶媒 1
実験手順
L-selectride (0.76 mL, 0.76 mmol, 1 M/THF) was added to a −78° C. THF (20 mL) solution of 10-3 (415 mg, 0.63 mmol). The reaction was stirred for 1 h and then 3% H2O2 (14 mL) was added. The resulting mixture was stirred at room temperature for 45 min. and then saturated NH4Cl solution (60 mL) was added. The resulting mixture was extracted with ethyl acetate (3×40 mL) and the combined ethyl acetate solution was washed with brine. The solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (25% ethyl acetate/hexanes) gave the title alcohol (255 mg, 0.39 mmol, 61%).
後処理
- stirringThe resulting mixture was stirred at room temperature for 45 min.
- extractionThe resulting mixture was extracted with ethyl acetate (3×40 mL)
- washthe combined ethyl acetate solution was washed with brine
- dry with materialThe solution was then dried (Na2SO4)
- filtrationfiltered
- customevaporated
- customPurification by flash chromatography on silica gel (25% ethyl acetate/hexanes)
出典と根拠
- ORDレコード
- ord-41d347d7d83e44799ee2817ae32e4c2a
- 出典データセット
- uspto-grants-2006_08
- 特許番号
- US07091231B2
関連ノート
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