(3aS,4R,5S,6aR)-(+)-六氢-5-羟基-4-(羟甲基)-2H-环戊并[b]呋喃-2-酮合成路线 （共 58 条）
反应条件
1: With trifluoroacetic acid T=50 - 80°C; 2 h; 2: With ammonium hydroxide in water pH=7; Product distribution / selectivity;
参考文献
ScinoPharm Taiwan, Ltd.
Patent: US2011/201809 A1, 2011 ;
Location in patent: Page/Page column 18 ;
反应条件
1: With trifluoroacetic acid T=50 - 60°C; 2 h; 2: With ammonium hydroxide in water pH=7; Product distribution / selectivity;
参考文献
ScinoPharm Taiwan, Ltd.
Patent: US2011/201809 A1, 2011 ;
Location in patent: Page/Page column 17 ;
反应条件
1: With sodium percarbonate in methanol Heating / reflux; 2: With acetic acid in methanol T=70 - 95°C; pH=6 - 7; 0.5 h; Product distribution / selectivity;
参考文献
Zhou, Maotang X.; Reiff, Emily A.; Vemishetti, Purushotham; Pendri, Yadagiri R.; Singh, Ambarish K.; Prasad, Siva Josyula; Dhokte, Ulhas P.; Qian, Xinhua; Mountford, Pia; Hartung, Kerry B.; Sailes, Helen
Patent: US2005/272932 A1, 2005 ;
Location in patent: Page/Page column 21 ;
反应条件
1: With sodium percarbonate in methanol Heating / reflux; 2: With sodium hydroxide; water in methanol T=70 - 75°C; pH=10 - 11; 3: With water; acetic acid in methanol T=70 - 75°C; pH=6 - 7; Product distribution / selectivity;
参考文献
Zhou, Maotang X.; Reiff, Emily A.; Vemishetti, Purushotham; Pendri, Yadagiri R.; Singh, Ambarish K.; Prasad, Siva Josyula; Dhokte, Ulhas P.; Qian, Xinhua; Mountford, Pia; Hartung, Kerry B.; Sailes, Helen
Patent: US2005/272932 A1, 2005 ;
Location in patent: Page/Page column 23-24 ;
反应条件
boron trichloride in dichloromethane T=-78°C;
参考文献
Bisacchi; Chao; Bachard; Daris; Innaimo; Jacobs; Kocy; Lapointe; Martel; Merchant; Slusarchyk; Sundeen; Young; Colonno; Zahler
Bioorganic and Medicinal Chemistry Letters, 1997 , vol. 7, # 2 p. 127 - 132
反应条件
1: With boron trichloride in dichloromethane T=-23 - -19°C; 3 h; 2: With methanol in dichloromethane; tert-butyl methyl ether T=-20 - 85°C; Activated carbonHeating / reflux; 3: With sodium hydroxide; water T=40°C; pH=7; Product distribution / selectivity;
参考文献
Zhou, Maotang X.; Reiff, Emily A.; Vemishetti, Purushotham; Pendri, Yadagiri R.; Singh, Ambarish K.; Prasad, Siva Josyula; Dhokte, Ulhas P.; Qian, Xinhua; Mountford, Pia; Hartung, Kerry B.; Sailes, Helen
Patent: US2005/272932 A1, 2005 ;
Location in patent: Page/Page column 19-20 ;
反应条件
hydrogenchloride in tetrahydrofuran; methanol; water T=55°C;
参考文献
Zhou, Bing; Li, Yuanchao
Tetrahedron Letters, 2012 , vol. 53, # 5 p. 502 - 504
反应条件
hydrogenchloride; water in tetrahydrofuran 6 h; Reflux;
参考文献
Liu, Xiaoyu; Jiao, Xiaozhen; Wu, Qian; Tian, Chengsen; Li, Renze; Xie, Ping
Tetrahedron Letters, 2012 , vol. 53, # 29 p. 3805 - 3807
反应条件
1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran 2: hydrogenchloride / tetrahydrofuran; methanol; water / 55 °C View Scheme
参考文献
Tetrahedron Letters, , vol. 53, # 5 p. 502 - 504
反应条件
1.1: BH3*S(CH3)2 / (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole / dichloromethane / 3 h / 0 °C 2.1: 1H-imidazole / dichloromethane / 2 h / 20 °C 3.1: dIpc2BH / tetrahydrofuran / 5 h / 0 - 20 °C 3.2: 1.75 h / 0 - 12 °C 4.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C 5.1: triethylamine / dichloromethane / 1 h / 0 - 5 °C 6.1: 3-chloro-benzenecarboperoxoic acid; disodium hydrogenphosphate / dichloromethane / 2.5 h / -25 °C 6.2: -25 - 20 °C 7.1: titanium tetrachloride / tetrahydrofuran / 3.5 h / -40 - 20 °C 8.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / -20 °C 9.1: toluene-4-sulfonic acid; methanol / 4 h / 0 - 20 °C 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C 11.1: sodium hydroxide; water / 3.5 h / 72 °C 11.2: 0 °C / pH 6.3 View Scheme
