反応式
[C:1]([O:4][CH:5]1[CH:10]([O:11][C:12](=[O:14])[CH3:13])[CH:9]([O:15][C:16](=[O:18])[CH3:17])[CH:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][CH:6]1[O:24][C:25]1[CH:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[S:27][C:26]=1[C:33](=O)[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)(=[O:3])[CH3:2].C[Si](C)(C)Cl.C([BH3-])#N.[Na+]>C(#N)C>[C:1]([O:4][CH:5]1[CH:10]([O:11][C:12](=[O:14])[CH3:13])[CH:9]([O:15][C:16](=[O:18])[CH3:17])[CH:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][CH:6]1[O:24][C:25]1[CH:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[S:27][C:26]=1[CH2:33][C:34]1[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=1)(=[O:3])[CH3:2]参加物
5
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 0 °C
実験手順
630 mg of (4,5-diacetoxy-6-acetoxymethyl-2-[5-isopropyl-2-(4-methoxy-benzoyl)-thiophen-3-yloxy]-tetrahydro-pyran-3-yl) acetate were dissolved in 30 ml of acetonitrile and cooled to 0° C. in an ice bath. 1.31 ml of trimethylchlorosilane and 652 mg of sodium cyanoborohydride were added, the ice bath was removed and the reaction was stirred for 2 h. 100 ml of water were added to the reaction mixture, which was extracted twice with 70 ml of dichloromethane each time. The combined organic phases were washed with 50 ml of saturated sodium chloride solution, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (SiO2, ethyl acetate/n-heptane=1:1).
後処理
- customthe ice bath was removed
- addition100 ml of water were added to the reaction mixture, which
- extractionwas extracted twice with 70 ml of dichloromethane each time
- washThe combined organic phases were washed with 50 ml of saturated sodium chloride solution
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe crude product was purified by column chromatography (SiO2, ethyl acetate/n-heptane=1:1)
出典と根拠
- ORDレコード
- ord-f73d86f60a234e4c8299a158556fc0b4
- 出典データセット
- uspto-grants-2010_02
- 特許番号
- US07666848B2
関連ノート
読み込み中…