(4Z,7S,8R,9E,11E,13Z,15E,17S,19Z)-7,8,17-三羟基-4,9,11,13,15,19-二十二碳六烯酸合成路线 (共 11 条)
→
872993-05-0(4Z,7S,8R,9E,11E,13Z,15E,17S,19Z)-7,8,17-三羟基-4,9,11,13,15,19-二十二碳六烯酸
反应条件
1: With water; lithium hydroxide hydrate in methanol
T=0°C; Inert atmosphere;
2: With sodium dihydrogenphosphate in ethyl acetate
Inert atmosphere;
参考文献
Rodriguez, Ana R.; Spur, Bernd W.
Tetrahedron Letters, 2012 , vol. 53, # 51 p. 6990 - 6994
→
872993-05-0(4Z,7S,8R,9E,11E,13Z,15E,17S,19Z)-7,8,17-三羟基-4,9,11,13,15,19-二十二碳六烯酸
反应条件
1.1: sodium hexamethyldisilazane / diethyl ether / -78 - 20 °C
2.1: iodine; triphenylphosphine; 1H-imidazole / toluene / 60 °C
3.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C
4.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; piperidine / benzene / 2 h / 20 °C / |Inert atmosphere; |Darkness
5.1: acetyl chloride; methanol / 0 °C
6.1: water / methanol / 5 h / 50 °C
7.1: water; lithium hydroxide hydrate / methanol / 0 °C / |Inert atmosphere
7.2: |Inert atmosphere
View Scheme
参考文献
Rodriguez, Ana R.; Spur, Bernd W.
Tetrahedron Letters, 2012 , vol. 53, # 51 p. 6990 - 6994
→
872993-05-0(4Z,7S,8R,9E,11E,13Z,15E,17S,19Z)-7,8,17-三羟基-4,9,11,13,15,19-二十二碳六烯酸
反应条件
1.1: iodine; triphenylphosphine; 1H-imidazole / toluene / 60 °C
2.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C
3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; piperidine / benzene / 2 h / 20 °C / |Inert atmosphere; |Darkness
4.1: acetyl chloride; methanol / 0 °C
5.1: water / methanol / 5 h / 50 °C
6.1: water; lithium hydroxide hydrate / methanol / 0 °C / |Inert atmosphere
6.2: |Inert atmosphere
View Scheme
参考文献
Rodriguez, Ana R.; Spur, Bernd W.
Tetrahedron Letters, 2012 , vol. 53, # 51 p. 6990 - 6994
→
872993-05-0(4Z,7S,8R,9E,11E,13Z,15E,17S,19Z)-7,8,17-三羟基-4,9,11,13,15,19-二十二碳六烯酸
反应条件
1.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C
2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; piperidine / benzene / 2 h / 20 °C / |Inert atmosphere; |Darkness
3.1: acetyl chloride; methanol / 0 °C
4.1: water / methanol / 5 h / 50 °C
5.1: water; lithium hydroxide hydrate / methanol / 0 °C / |Inert atmosphere
5.2: |Inert atmosphere
View Scheme
参考文献
Rodriguez, Ana R.; Spur, Bernd W.
Tetrahedron Letters, 2012 , vol. 53, # 51 p. 6990 - 6994
→
872993-05-0(4Z,7S,8R,9E,11E,13Z,15E,17S,19Z)-7,8,17-三羟基-4,9,11,13,15,19-二十二碳六烯酸
反应条件
1.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; piperidine / benzene / 2 h / 20 °C / |Inert atmosphere; |Darkness
2.1: acetyl chloride; methanol / 0 °C
3.1: water / methanol / 5 h / 50 °C
4.1: water; lithium hydroxide hydrate / methanol / 0 °C / |Inert atmosphere
4.2: |Inert atmosphere
View Scheme
参考文献
Rodriguez, Ana R.; Spur, Bernd W.
Tetrahedron Letters, 2012 , vol. 53, # 51 p. 6990 - 6994
→
872993-05-0(4Z,7S,8R,9E,11E,13Z,15E,17S,19Z)-7,8,17-三羟基-4,9,11,13,15,19-二十二碳六烯酸
反应条件
1.1: Dess-Martin periodane / dichloromethane / 20 °C
2.1: n-butyllithium / tetrahydrofuran / -78 - 0 °C
3.1: iodine / benzene / 20 °C
4.1: KF*2H2O; 18-crown-6 ether / N,N-dimethyl-formamide / 20 °C
5.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; piperidine / benzene / 2 h / 20 °C / |Inert atmosphere; |Darkness
6.1: acetyl chloride; methanol / 0 °C
7.1: water / methanol / 5 h / 50 °C
8.1: water; lithium hydroxide hydrate / methanol / 0 °C / |Inert atmosphere
8.2: |Inert atmosphere
View Scheme
参考文献
Rodriguez, Ana R.; Spur, Bernd W.
Tetrahedron Letters, 2012 , vol. 53, # 51 p. 6990 - 6994
→
872993-05-0(4Z,7S,8R,9E,11E,13Z,15E,17S,19Z)-7,8,17-三羟基-4,9,11,13,15,19-二十二碳六烯酸
反应条件
1.1: acetyl chloride; methanol / 0 °C
2.1: water / methanol / 5 h / 50 °C
3.1: water; lithium hydroxide hydrate / methanol / 0 °C / |Inert atmosphere
3.2: |Inert atmosphere
View Scheme
参考文献
Rodriguez, Ana R.; Spur, Bernd W.
Tetrahedron Letters, 2012 , vol. 53, # 51 p. 6990 - 6994
→
872993-05-0(4Z,7S,8R,9E,11E,13Z,15E,17S,19Z)-7,8,17-三羟基-4,9,11,13,15,19-二十二碳六烯酸
反应条件
1.1: water / methanol / 5 h / 50 °C
2.1: water; lithium hydroxide hydrate / methanol / 0 °C / |Inert atmosphere
2.2: |Inert atmosphere
View Scheme
参考文献
Rodriguez, Ana R.; Spur, Bernd W.
Tetrahedron Letters, 2012 , vol. 53, # 51 p. 6990 - 6994
→
872993-05-0(4Z,7S,8R,9E,11E,13Z,15E,17S,19Z)-7,8,17-三羟基-4,9,11,13,15,19-二十二碳六烯酸
反应条件
1.1: n-butyllithium / tetrahydrofuran / -78 - 0 °C
2.1: iodine / benzene / 20 °C
3.1: KF*2H2O; 18-crown-6 ether / N,N-dimethyl-formamide / 20 °C
4.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; piperidine / benzene / 2 h / 20 °C / |Inert atmosphere; |Darkness
5.1: acetyl chloride; methanol / 0 °C
6.1: water / methanol / 5 h / 50 °C
7.1: water; lithium hydroxide hydrate / methanol / 0 °C / |Inert atmosphere
7.2: |Inert atmosphere
View Scheme
参考文献
Rodriguez, Ana R.; Spur, Bernd W.
Tetrahedron Letters, 2012 , vol. 53, # 51 p. 6990 - 6994
→
872993-05-0(4Z,7S,8R,9E,11E,13Z,15E,17S,19Z)-7,8,17-三羟基-4,9,11,13,15,19-二十二碳六烯酸
反应条件
1.1: KF*2H2O; 18-crown-6 ether / N,N-dimethyl-formamide / 20 °C
2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; piperidine / benzene / 2 h / 20 °C / |Inert atmosphere; |Darkness
3.1: acetyl chloride; methanol / 0 °C
4.1: water / methanol / 5 h / 50 °C
5.1: water; lithium hydroxide hydrate / methanol / 0 °C / |Inert atmosphere
5.2: |Inert atmosphere
View Scheme
参考文献
Rodriguez, Ana R.; Spur, Bernd W.
Tetrahedron Letters, 2012 , vol. 53, # 51 p. 6990 - 6994