Hexane → HCID 13891111、化合物
反応式
C([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH:10]([OH:13])[CH:11]=[CH2:12])=O)(C)(C)C.[H-].[Na+].CCCCCC>CN(C)C=O>[CH:15]1([CH2:14][C@H:9]2[CH:10]([CH:11]=[CH2:12])[O:13][C:6](=[O:5])[NH:8]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1参加物
5
実験手順
The resultant product of Example 17 (2.80 g, 9.88 mmol) in dry dimethylformamide (OMF) (50 ml) was added to a stirred suspension of NaH (593 mg of a 60% dispersion in oil, 14.8 mmol, hexane washed) in dry DMF (50 ml). After 3 h, the mixture was quenched (750 ml water+100 ml brine) and extracted with ether (5×100 ml). The combined organic phase was washed with brine (3×50 ml), dried (MgSO4), filtered and evaporated to an oil (2.23 g). The NMR spectrum of the crude product revealed an 82:18 mixture of 5S:5R diastereomers. Silica gel chromatography gave 80% recovery of pure diastereomers. 5S: