甲基(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7-二乙酰氧基-12-羟基-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-17-基]戊酸酯合成路线 （共 9 条）
3749-87-9甲基(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7-二乙酰氧基-12-羟基-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-17-基]戊酸酯
→
反应条件
1: chromium (VI)-oxide; acetic acid 2: methanol. KOH-solution View Scheme
参考文献
Helvetica Chimica Acta, , vol. 30, p. 1542,1552
3749-87-9甲基(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7-二乙酰氧基-12-羟基-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-17-基]戊酸酯
→
反应条件
potassium-sodium; Sec-butyl alcohol; tri[2-(2-methoxyethoxy)ethyl]amine in tetrahydrofuran Ambient temperaturevar. cat.: 18-crown-6; Yields of byproduct given;
参考文献
Bose, Ajay K.; Mangiaracina, Pietro
Tetrahedron Letters, 1987 , vol. 28, # 22 p. 2503 - 2506
3749-87-9甲基(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7-二乙酰氧基-12-羟基-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-17-基]戊酸酯
→
反应条件
potassium-sodium; Sec-butyl alcohol; 18-crown-6 ether in tetrahydrofuran Ambient temperaturevar. cat.: tris(3,6-dioxaheptyl)amine;
参考文献
Tetrahedron Letters, , vol. 28, # 22 p. 2503 - 2506
3749-87-9甲基(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7-二乙酰氧基-12-羟基-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-17-基]戊酸酯
→
反应条件
1: acetic acid; sodium hypochlorite / ethyl acetate / 30 - 40 °C / |Large scale 2: hydrazine hydrate; potassium hydroxide / 1,2-bis-(2-hydroxyethoxy)-ethane / 4 h / 120 - 210 °C / |Large scale 3: sulfuric acid; sodium bromide; Sodium bromate; water / butan-1-ol; dichloromethane / 0 - 55 °C / |Large scale View Scheme
参考文献
ERREGIERRE S.P.A.; FERRARI, Massimo; ZINETTI, Fabrizio
Patent: WO2014/20024 A1, 2014 ;
3749-87-9甲基(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7-二乙酰氧基-12-羟基-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-17-基]戊酸酯
→
反应条件
1: methanol. HCl 2: K2cro4; aqueous acetic acid 3: KOH; triethylene glycol / weiteres Reagens: N2H4 View Scheme
参考文献
ERREGIERRE S.P.A.; FERRARI, Massimo; ZINETTI, Fabrizio
Patent: WO2014/20024 A1, 2014 ;
3749-87-9甲基(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7-二乙酰氧基-12-羟基-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-17-基]戊酸酯
→
反应条件
1.1: acetic acid; sodium hypochlorite / ethyl acetate / 30 - 40 °C / |Large scale 2.1: hydrazine hydrate; potassium hydroxide / 1,2-bis-(2-hydroxyethoxy)-ethane / 4 h / 120 - 210 °C / |Large scale 3.1: sulfuric acid; sodium bromide; Sodium bromate; water / butan-1-ol; dichloromethane / 0 - 55 °C / |Large scale 4.1: sodium / Sec-butyl alcohol / 0.5 h / |Reflux; |Large scale 4.2: 30 °C / |Large scale 4.3: |Large scale 5.1: water; phosphoric acid / Sec-butyl alcohol / 70 °C / |Large scale 5.2: 2 h / |Reflux; |Large scale View Scheme
3749-87-9甲基(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7-二乙酰氧基-12-羟基-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-17-基]戊酸酯
→
反应条件
potassium-sodium; Sec-butyl alcohol; tri[2-(2-methoxyethoxy)ethyl]amine in tetrahydrofuran Ambient temperaturevar. cat.: 18-crown-6; Yield given. Yields of byproduct given;
参考文献
Bose, Ajay K.; Mangiaracina, Pietro
Tetrahedron Letters, 1987 , vol. 28, # 22 p. 2503 - 2506
3749-87-9甲基(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7-二乙酰氧基-12-羟基-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-17-基]戊酸酯
→
反应条件
potassium-sodium; Sec-butyl alcohol; tri[2-(2-methoxyethoxy)ethyl]amine in tetrahydrofuran Ambient temperaturevar. cat.: 18-crown-6; Yields of byproduct given;
参考文献
Bose, Ajay K.; Mangiaracina, Pietro
Tetrahedron Letters, 1987 , vol. 28, # 22 p. 2503 - 2506
3749-87-9甲基(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7-二乙酰氧基-12-羟基-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-17-基]戊酸酯
→
反应条件
1.1: acetic acid; sodium hypochlorite / ethyl acetate / 30 - 40 °C / |Large scale 2.1: hydrazine hydrate; potassium hydroxide / 1,2-bis-(2-hydroxyethoxy)-ethane / 4 h / 120 - 210 °C / |Large scale 3.1: sulfuric acid; sodium bromide; Sodium bromate; water / butan-1-ol; dichloromethane / 0 - 55 °C / |Large scale 4.1: sodium / Sec-butyl alcohol / 0.5 h / |Reflux; |Large scale 4.2: 30 °C / |Large scale 4.3: |Large scale 5.1: water; phosphoric acid / Sec-butyl alcohol / 70 °C / |Large scale 5.2: 2 h / |Reflux; |Large scale 6.1: water; sodium hydroxide / 2 h / 97 °C / |Large scale View Scheme
参考文献
ERREGIERRE S.P.A.; FERRARI, Massimo; ZINETTI, Fabrizio
Patent: WO2014/20024 A1, 2014 ;
