4-[(1E,3S,5Z,8R/S,10S)-3,11-二-{[叔-丁基(二甲基)硅烷基]氧基}-2,6,10-三甲基-8-(苯磺酰基)十一碳-1,5-二烯基]-2-甲基-1,3-噻唑合成路线 (共 18 条)
反应条件
1: (-)-(3S)-4-{[tert-butyl(dimethyl)silyl]oxy}-3-methylbutyl phenyl sulfone With 18-crown-6 ether; potassium hexamethylsilazane in tetrahydrofuran T=-78°C; 1 h; 2: 4-((1E,3S,5Z)-3-{[tert-butyl(dimethyl)silyl]oxy}-7-iodo-2,6-dimethylhepta-1,5-dienyl)-2-methyl-1,3-thiazole in tetrahydrofuran T=-78°C; 1 h; Further stages.;
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
Journal of Organic Chemistry, 2000 , vol. 65, # 22 p. 7456 - 7467
反应条件
1.1: 4.96 g / tetrahydrofuran; diethyl ether / 1.5 h / -78 °C 2.1: 10.95 g / LiHMDS / tetrahydrofuran / 0.67 h / 55 °C 3.1: oxalyl chloride; DMSO; DIPEA / CH2Cl2 / -78 - 20 °C 4.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.25 h 4.2: 5.45 g / tetrahydrofuran / 0.5 h / -78 °C 5.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C 6.1: Ph3P; imidazole; I2 / acetonitrile; diethyl ether / 1 h / 20 °C 7.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 7.2: 93 percent / tetrahydrofuran / 1 h / -78 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 65, # 22 p. 7456 - 7467
反应条件
1.1: oxalyl chloride; DMSO; DIPEA / CH2Cl2 / -78 - 20 °C 2.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.25 h 2.2: 5.45 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C 4.1: Ph3P; imidazole; I2 / acetonitrile; diethyl ether / 1 h / 20 °C 5.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 5.2: 93 percent / tetrahydrofuran / 1 h / -78 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 65, # 22 p. 7456 - 7467
反应条件
1.1: 10.95 g / LiHMDS / tetrahydrofuran / 0.67 h / 55 °C 2.1: oxalyl chloride; DMSO; DIPEA / CH2Cl2 / -78 - 20 °C 3.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.25 h 3.2: 5.45 g / tetrahydrofuran / 0.5 h / -78 °C 4.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C 5.1: Ph3P; imidazole; I2 / acetonitrile; diethyl ether / 1 h / 20 °C 6.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 6.2: 93 percent / tetrahydrofuran / 1 h / -78 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 65, # 22 p. 7456 - 7467
反应条件
1.1: Ph3P; imidazole; I2 / acetonitrile; diethyl ether / 1 h / 20 °C 2.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 2.2: 93 percent / tetrahydrofuran / 1 h / -78 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 65, # 22 p. 7456 - 7467
反应条件
1.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C 2.1: Ph3P; imidazole; I2 / acetonitrile; diethyl ether / 1 h / 20 °C 3.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 3.2: 93 percent / tetrahydrofuran / 1 h / -78 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 65, # 22 p. 7456 - 7467
反应条件
1.1: 97 percent / benzene / 8 h / Heating 2.1: 10.95 g / LiHMDS / tetrahydrofuran / 0.67 h / 55 °C 3.1: oxalyl chloride; DMSO; DIPEA / CH2Cl2 / -78 - 20 °C 4.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.25 h 4.2: 5.45 g / tetrahydrofuran / 0.5 h / -78 °C 5.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C 6.1: Ph3P; imidazole; I2 / acetonitrile; diethyl ether / 1 h / 20 °C 7.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 7.2: 93 percent / tetrahydrofuran / 1 h / -78 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 65, # 22 p. 7456 - 7467
反应条件
1.1: 99 percent / imidazole / dimethylformamide / 3 h / 0 - 20 °C 2.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 2.2: 93 percent / tetrahydrofuran / 1 h / -78 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 65, # 22 p. 7456 - 7467
反应条件
1.1: 99 percent / imidazole / dimethylformamide / 3 h / 0 - 20 °C 2.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 2.2: 93 percent / tetrahydrofuran / 1 h / -78 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 65, # 22 p. 7456 - 7467
反应条件
1.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.25 h 1.2: 5.45 g / tetrahydrofuran / 0.5 h / -78 °C 2.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C 3.1: Ph3P; imidazole; I2 / acetonitrile; diethyl ether / 1 h / 20 °C 4.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 4.2: 93 percent / tetrahydrofuran / 1 h / -78 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 65, # 22 p. 7456 - 7467