Ipragliflozin; (1S)-1,5-脱水-1-C-[3-[(1-苯并噻吩-2-基)甲基]-4-氟苯基]-D-葡糖醇合成路线 (共 6 条)
反应条件
1: With boron trichloride in n-heptane; dichloromethane; C6HMe5 T=-78°C; 3 h; Inert atmosphere; 2: With methanol in n-heptane; dichloromethane; C6HMe5 T=-78°C;
参考文献
Astellas Pharma Inc.; Kotobuki Pharmaceutical Co., Ltd.
Patent: EP2105442 A1, 2009 ;
Location in patent: Page/Page column 13 ;
反应条件
1: With methanol; water; sodium hydroxide T=25 - 49.1°C; 2: With hydrogenchloride in methanol; water T=20.2 - 60°C;
参考文献
Astellas Pharma Inc.; Kotobuki Pharmaceutical Co., Ltd.
Patent: EP2105442 A1, 2009 ;
Location in patent: Page/Page column 15 ;
反应条件
1.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.17 h / -78 °C 2.2: 2 h / -78 °C 3.1: C6HMe5; boron trichloride / n-heptane; dichloromethane / 4 h / -78 °C 3.2: -78 - 20 °C View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 20, # 10 p. 3263 - 3279
反应条件
1.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.17 h / -78 °C 1.2: 2 h / -78 °C 2.1: C6HMe5; boron trichloride / n-heptane; dichloromethane / 4 h / -78 °C 2.2: -78 - 20 °C View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 20, # 10 p. 3263 - 3279
反应条件
1.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 1.2: 2 h / -78 °C 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.17 h / -78 °C 3.2: 2 h / -78 °C 4.1: C6HMe5; boron trichloride / n-heptane; dichloromethane / 4 h / -78 °C 4.2: -78 - 20 °C View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 20, # 10 p. 3263 - 3279
反应条件
1.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C 1.2: 2 h / -78 °C 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.17 h / -78 °C 3.2: 2 h / -78 °C 4.1: C6HMe5; boron trichloride / n-heptane; dichloromethane / 4 h / -78 °C 4.2: -78 - 20 °C View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 20, # 10 p. 3263 - 3279