(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸 合成路线 (共 69 条)
→
反应条件
193146-63-3 (3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
1.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C
2.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C
2.2: 3 h / 5 °C
View Scheme
参考文献
Hurski; Kulinkovich
Russian Journal of Organic Chemistry, 2011 , vol. 47, # 11 p. 1653 - 1674
→
反应条件
193146-63-3 (3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
1.1: triethylamine / diethyl ether / 0 °C
2.1: magnesium; ethylene dibromide / diethyl ether / 0.37 h / 20 °C / Cooling
2.2: 0.53 h / 20 °C
2.3: 14 h / 20 °C
3.1: pyridinium p-toluenesulfonate; dimethyl sulfoxide / 4 h / 65 °C
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C
4.2: -78 - 0 °C
5.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C
5.2: 0.08 h / -78 °C
6.1: formic acid / diethyl ether / 10 h / 5 - 20 °C
7.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C
8.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C
8.2: 3 h / 5 °C
View Scheme
参考文献
Hurski; Kulinkovich
Russian Journal of Organic Chemistry, 2011 , vol. 47, # 11 p. 1653 - 1674
→
反应条件
193146-63-3 (3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
1.1: magnesium; ethylene dibromide / diethyl ether / 0.37 h / 20 °C / Cooling
1.2: 0.53 h / 20 °C
1.3: 14 h / 20 °C
2.1: pyridinium p-toluenesulfonate; dimethyl sulfoxide / 4 h / 65 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C
3.2: -78 - 0 °C
4.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C
4.2: 0.08 h / -78 °C
5.1: formic acid / diethyl ether / 10 h / 5 - 20 °C
6.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C
7.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C
7.2: 3 h / 5 °C
View Scheme
参考文献
Hurski; Kulinkovich
Russian Journal of Organic Chemistry, 2011 , vol. 47, # 11 p. 1653 - 1674
→
反应条件
193146-63-3 (3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
1.1: pyridine; 4-(N,N-dimethlyamino)pyridine / 3 h / -20 - 5 °C
1.2: 5 °C
2.1: magnesium; ethylene dibromide; N-ethyl-N,N-diisopropylamine / diethyl ether; toluene / 2 h / 100 °C
3.1: n-butyllithium / diethyl ether; hexane / 3 h / -78 °C
3.2: 20 °C
3.3: 0.08 h / 0 °C
4.1: potassium tert-butylate / tert-butyl alcohol / 1 h / Reflux
4.2: 1 h / Reflux
5.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 5 °C
6.1: dimethylsulfide borane complex; (+)-(1R,5R)-α-pinene / tetrahydrofuran / 0 - 20 °C
6.2: 2 h / 20 °C
7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C
7.2: -78 - 0 °C
8.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C
8.2: 0.08 h / -78 °C
9.1: formic acid / diethyl ether / 10 h / 5 - 20 °C
10.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C
11.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C
11.2: 3 h / 5 °C
View Scheme
参考文献
Hurski; Kulinkovich
Russian Journal of Organic Chemistry, 2011 , vol. 47, # 11 p. 1653 - 1674
→
反应条件
193146-63-3 (3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
1.1: magnesium; ethylene dibromide; N-ethyl-N,N-diisopropylamine / diethyl ether; toluene / 2 h / 100 °C
2.1: n-butyllithium / diethyl ether; hexane / 3 h / -78 °C
2.2: 20 °C
2.3: 0.08 h / 0 °C
3.1: potassium tert-butylate / tert-butyl alcohol / 1 h / Reflux
3.2: 1 h / Reflux
4.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 5 °C
5.1: dimethylsulfide borane complex; (+)-(1R,5R)-α-pinene / tetrahydrofuran / 0 - 20 °C
5.2: 2 h / 20 °C
6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C
6.2: -78 - 0 °C
7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C
7.2: 0.08 h / -78 °C
8.1: formic acid / diethyl ether / 10 h / 5 - 20 °C
9.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C
10.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C
10.2: 3 h / 5 °C
View Scheme
参考文献
Hurski; Kulinkovich
Russian Journal of Organic Chemistry, 2011 , vol. 47, # 11 p. 1653 - 1674
→
反应条件
193146-63-3 (3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
1.1: n-butyllithium / diethyl ether; hexane / 3 h / -78 °C
1.2: 20 °C
1.3: 0.08 h / 0 °C
2.1: potassium tert-butylate / tert-butyl alcohol / 1 h / Reflux
2.2: 1 h / Reflux
3.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 5 °C
4.1: dimethylsulfide borane complex; (+)-(1R,5R)-α-pinene / tetrahydrofuran / 0 - 20 °C
4.2: 2 h / 20 °C
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C
5.2: -78 - 0 °C
6.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C
6.2: 0.08 h / -78 °C
7.1: formic acid / diethyl ether / 10 h / 5 - 20 °C
8.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C
9.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C
9.2: 3 h / 5 °C
View Scheme
参考文献
Hurski; Kulinkovich
Russian Journal of Organic Chemistry, 2011 , vol. 47, # 11 p. 1653 - 1674
→
反应条件
193146-63-3 (3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
1.1: potassium tert-butylate / tert-butyl alcohol / 1 h / Reflux
1.2: 1 h / Reflux
2.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 5 °C
3.1: dimethylsulfide borane complex; (+)-(1R,5R)-α-pinene / tetrahydrofuran / 0 - 20 °C
3.2: 2 h / 20 °C
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C
4.2: -78 - 0 °C
5.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C
5.2: 0.08 h / -78 °C
6.1: formic acid / diethyl ether / 10 h / 5 - 20 °C
7.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C
8.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C
8.2: 3 h / 5 °C
View Scheme
参考文献
Hurski; Kulinkovich
Russian Journal of Organic Chemistry, 2011 , vol. 47, # 11 p. 1653 - 1674
→
反应条件
193146-63-3 (3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
1.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 5 °C
2.1: dimethylsulfide borane complex; (+)-(1R,5R)-α-pinene / tetrahydrofuran / 0 - 20 °C
2.2: 2 h / 20 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C
3.2: -78 - 0 °C
4.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C
4.2: 0.08 h / -78 °C
5.1: formic acid / diethyl ether / 10 h / 5 - 20 °C
6.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C
7.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C
7.2: 3 h / 5 °C
View Scheme
参考文献
Hurski; Kulinkovich
Russian Journal of Organic Chemistry, 2011 , vol. 47, # 11 p. 1653 - 1674
→
反应条件
193146-63-3 (3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸
反应条件
1.1: dimethylsulfide borane complex; (+)-(1R,5R)-α-pinene / tetrahydrofuran / 0 - 20 °C
1.2: 2 h / 20 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C
2.2: -78 - 0 °C
3.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C
3.2: 0.08 h / -78 °C
4.1: formic acid / diethyl ether / 10 h / 5 - 20 °C
5.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C
6.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C
6.2: 3 h / 5 °C
View Scheme
参考文献
Hurski; Kulinkovich
Russian Journal of Organic Chemistry, 2011 , vol. 47, # 11 p. 1653 - 1674