Triisopropyl phosphite → HCID 54076213, 화합물
반응식
[C:1]([O:4][CH2:5][CH2:6][C:7]([CH2:18]Br)=[CH:8][C@@H:9]([NH:15][CH:16]=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:3])[CH3:2].[P:20]([O:29]C(C)C)([O:25][CH:26]([CH3:28])[CH3:27])[O:21][CH:22]([CH3:24])[CH3:23]>>[C:1]([O:4][CH2:5][CH2:6][C:7]([CH2:18][P:20]([O:25][CH:26]([CH3:28])[CH3:27])([O:21][CH:22]([CH3:24])[CH3:23])=[O:29])=[CH:8][C@@H:9]([NH:15][CH:16]=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:3])[CH3:2]참가 물질
3
실험 절차
21.2 g (63.1 mmol) of ethyl 6-acetoxy-4-bromomethyl-2(R)-formylamino-hex-3-enoate and 69.1 ml (252.2 mmol) of 90% triisopropyl phosphite are heated to 80° C. and the mixture is stirred for 18 hours under a pressure of 100-150 mbar. Excess triisopropyl phosphite is removed by distillation and the residue is purified by flash chromatography on silica gel with ethyl acetate/ethanol (19:1), giving 8.6 g of ethyl 6-acetoxy-2(R)-formylamino-4-diisopropylphosphonomethyl-hex-3-enoate a yellowish-orange oil. ee=92.5%; αD -90.2°±0.4° (c=2.84 CH2Cl2).
후처리
- customExcess triisopropyl phosphite is removed by distillation
- customthe residue is purified by flash chromatography on silica gel with ethyl acetate/ethanol (19:1)