5-{[二甲基(2-甲基-2-丙基)硅烷基]氧基}-2-氧代六氢-2H-环戊二烯并[b]呋喃-4-甲醛合成路线 （共 9 条）
反应条件
1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / Inert atmosphere 1.2: 1.5 h / 0 °C 2.1: B-chloro-diisopinocampheylborane / n-heptane; tetrahydrofuran / 5 h / -30 - -25 °C / Inert atmosphere 2.2: 10 h / 20 °C 3.1: triethylamine; hydrogen / palladium 10 on activated carbon / tetrahydrofuran / 1 h / 20 °C / 760.05 Torr 4.1: 1H-imidazole / dichloromethane / 18 h / 20 °C 5.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.5 h / -30 °C / Inert atmosphere 5.2: -30 °C 6.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 6.2: 3.25 h / 0 - 20 °C 7.1: hydrogenchloride / water; tetrahydrofuran / 18 h / 20 °C 7.2: pH 6.8 / Aqueous phosphate buffer View Scheme
参考文献
Biffi, Giancarlo; D'Alfonso, Alessandro; Feliciani, Lazzaro; Porta, Alessio; Vidari, Giovanni; Viscardi, Enrico; Zanoni, Giuseppe
Patent: US2012/16136 A1, 2012 ;
反应条件
1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / Inert atmosphere 1.2: 1.5 h / 0 °C 2.1: B-chloro-diisopinocampheylborane / n-heptane; tetrahydrofuran / 5 h / -30 - -25 °C / Inert atmosphere 2.2: 10 h / 20 °C 3.1: triethylamine; hydrogen / palladium 10 on activated carbon / tetrahydrofuran / 1 h / 20 °C / 760.05 Torr 4.1: 1H-imidazole / dichloromethane / 18 h / 20 °C 5.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.5 h / -30 °C / Inert atmosphere 5.2: -30 °C 6.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 6.2: 3.25 h / 0 - 20 °C 7.1: hydrogenchloride / water; tetrahydrofuran / 18 h / 20 °C 7.2: pH 6.8 / Aqueous phosphate buffer 8.1: Novozym 435 / 18 h / 30 °C View Scheme
参考文献
Biffi, Giancarlo; D'Alfonso, Alessandro; Feliciani, Lazzaro; Porta, Alessio; Vidari, Giovanni; Viscardi, Enrico; Zanoni, Giuseppe
Patent: US2012/16136 A1, 2012 ;
反应条件
1: KOtBu / tetrahydrofuran 2: 84 percent / Grubbs' 2nd generation catalyst / CH2Cl2 / 12 h / 40 °C 3: DIBAL-H / CH2Cl2 / -78 °C 4: KOtBu / tetrahydrofuran 5: HCl / tetrahydrofuran / 48 h View Scheme
参考文献
Sheddan, Neil A.; Arion, Vladimir B.; Mulzer, Johann
Tetrahedron Letters, 2006 , vol. 47, # 37 p. 6689 - 6693
反应条件
1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / Inert atmosphere 1.2: 1.5 h / 0 °C 2.1: B-chloro-diisopinocampheylborane / n-heptane; tetrahydrofuran / 5 h / -30 - -25 °C / Inert atmosphere 2.2: 10 h / 20 °C 3.1: 1H-imidazole / dichloromethane / 18 h / 20 °C 4.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.5 h / -30 °C / Inert atmosphere 4.2: -30 °C 5.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 5.2: 3.25 h / 0 - 20 °C 6.1: potassium carbonate / acetone / 18 h / 20 °C 7.1: water / tetrahydrofuran / 52 h / 20 °C 8.1: hydrogenchloride / water; tetrahydrofuran / 18 h / 20 °C 8.2: pH 6.8 / Aqueous phosphate buffer View Scheme
参考文献
Biffi, Giancarlo; D'Alfonso, Alessandro; Feliciani, Lazzaro; Porta, Alessio; Vidari, Giovanni; Viscardi, Enrico; Zanoni, Giuseppe
Patent: US2012/16136 A1, 2012 ;
反应条件
sodium hydrogencarbonate; Dess-Martin periodane in dichloromethane
Dess-Martin oxidation;
参考文献
Sheddan, Neil A.; Arion, Vladimir B.; Mulzer, Johann
Tetrahedron Letters, 2006 , vol. 47, # 37 p. 6689 - 6693
反应条件
1: K2CO3 / methanol
2: imidazole / dimethylformamide
3: Et2AlCl / CH2Cl2 / 2 h / -50 °C
4: Dess-Martin periodinane; NaHCO3 / CH2Cl2
View Scheme
参考文献
Sheddan, Neil A.; Arion, Vladimir B.; Mulzer, Johann
Tetrahedron Letters, 2006 , vol. 47, # 37 p. 6689 - 6693
反应条件
1: Et2AlCl / CH2Cl2 / 2 h / -50 °C
2: Dess-Martin periodinane; NaHCO3 / CH2Cl2
View Scheme
参考文献
Sheddan, Neil A.; Arion, Vladimir B.; Mulzer, Johann
Tetrahedron Letters, 2006 , vol. 47, # 37 p. 6689 - 6693
反应条件
1: 95 percent / DMAP; Et3N / CH2Cl2
2: K2CO3 / methanol
3: imidazole / dimethylformamide
4: Et2AlCl / CH2Cl2 / 2 h / -50 °C
5: Dess-Martin periodinane; NaHCO3 / CH2Cl2
View Scheme
参考文献
Sheddan, Neil A.; Arion, Vladimir B.; Mulzer, Johann
Tetrahedron Letters, 2006 , vol. 47, # 37 p. 6689 - 6693
反应条件
1: imidazole / dimethylformamide
2: Et2AlCl / CH2Cl2 / 2 h / -50 °C
3: Dess-Martin periodinane; NaHCO3 / CH2Cl2
View Scheme
参考文献
Sheddan, Neil A.; Arion, Vladimir B.; Mulzer, Johann
Tetrahedron Letters, 2006 , vol. 47, # 37 p. 6689 - 6693
