反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([NH:18][C@@H:19]([CH2:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[C@@H:20]([O:23][Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])[CH2:21][OH:22])=[O:17])([CH3:14])([CH3:13])[CH3:12].CCN(CC)CC>O1CCCC1.O>[C:11]([O:15][C:16]([NH:18][C@@H:19]([CH2:34][CH:35]1[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1)[C@@H:20]([O:23][Si:24]([CH:25]([CH3:26])[CH3:27])([CH:28]([CH3:29])[CH3:30])[CH:31]([CH3:32])[CH3:33])[CH:21]=[O:22])=[O:17])([CH3:12])([CH3:13])[CH3:14]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 2
実験手順
To a -78° C. solution of oxalyl chloride (10.8 mmol) in tetrahydrofuran (45 mL) was added dimethylsulfoxide (21.6 mmol). After stirring for 10 minutes, a solution of the title alcohol of Step 3 (10.8 mmol) in tetrahydrofuran (4.6 mL) was added dropwise. The solution was stirred for 20 minutes at -78° C. and then Et3N (45.1 mmol) was added. The reaction solution as allowed to warm to room temperature over a 2 hour period. The opaque, white mixture was poured into water (50 mL) and then extracted with ether (2×50 mL). The combined organic layer was washed with 1N HCl (50 mL), aqueous 5% NaHCO3 (50 mL), and brine (50 mL). The dried filtrate (MgSO4) was evaporated to give the title aldehyde (4.20 g, 100% yield). The 1H, 13C and APT NMR spectral data were consistent with the proposed structure.
後処理
- stirringThe solution was stirred for 20 minutes at -78° C.
- extractionextracted with ether (2×50 mL)
- washThe combined organic layer was washed with 1N HCl (50 mL), aqueous 5% NaHCO3 (50 mL), and brine (50 mL)
- customThe dried filtrate (MgSO4) was evaporated
出典と根拠
- ORDレコード
- ord-884fd87914404dd3b3a5827d4b2cf78b
- 出典データセット
- uspto-grants-1996_01
- 特許番号
- US05484812
関連ノート
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