(3S,4S)-1-[1-(allyloxycarbonyl)-1-(triphenylphosphoranediyl)methyl]-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine → allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
反応式
[CH2:1]([O:4][C:5]([C:7]([N:27]1[C@H:30]([C@H:31]([C:33]([S:35][CH3:36])=S)[CH3:32])[C@@H:29]([C@H:37]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH3:38])[C:28]1=[O:47])=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:6])[CH:2]=[CH2:3]>C1(C)C=CC=CC=1>[Si:40]([O:39][C@@H:37]([C@H:29]1[C:28](=[O:47])[N:27]2[C@@H:30]1[C@@H:31]([CH3:32])[C:33]([S:35][CH3:36])=[C:7]2[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[CH3:38])([C:43]([CH3:45])([CH3:44])[CH3:46])([CH3:41])[CH3:42]参加物
3
反応物 1
生成物 1
試薬・触媒・溶媒 1
実験手順
A solution of (3S,4S)-1-[1-(allyloxycarbonyl)-1-(triphenylphosphoranediyl)methyl]-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine (325 mg) in toluene (3 ml) was heated under reflux for 4.5 hours. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography [ethyl acetate-hexane (1:3, V/V)] to afford allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (164 mg).