(3aR,4S,5R,6aS)-(-)-六氢-4-(羟甲基)-2-氧代-2H-环戊并[b]呋喃-5-基 1,1'-联苯-4-甲酸酯合成路线 (共 14 条)
反应条件
sulfuric acid in methanol 14 h; Heating;
参考文献
Zak, Bohumil; Vesely, Ivan; Neumitka, Karel; Palecek, Jaroslav
Collection of Czechoslovak Chemical Communications, 1991 , vol. 56, # 8 p. 1690 - 1700
反应条件
sulfuric acid in methanol 14 h; Heating;
参考文献
Zak, Bohumil; Vesely, Ivan; Neumitka, Karel; Palecek, Jaroslav
Collection of Czechoslovak Chemical Communications, 1991 , vol. 56, # 8 p. 1690 - 1700
参考文献
Collection of Czechoslovak Chemical Communications, , vol. 57, # 2 p. 357 - 361
反应条件
1.1: Dess-Martin periodane / dichloromethane / 5 - 20 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0 - 5 °C 2.2: 1 h / 15 - 20 °C 2.3: 5 - 10 °C 3.1: B-chloro-diisopinocampheylborane / tetrahydrofuran / -25 - 0 °C 4.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 5 - 20 °C 5.1: potassium carbonate / methanol View Scheme
参考文献
LUPIN LIMITED; KAMMILI, Venkata, Rambabu; SMART, Anurag, Anil; SIYAN, Rajinder, Singh; BHISE, Nandu, Baban; SINGH, Girij, Pal
Patent: WO2013/164729 A1, 2013 ;
反应条件
1: DCC, phosphoric acid / 1,2-dimethoxy-ethane / a) 18 deg C, 30 min, b) RT, 2 h 2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h 3: 52 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C 4: 78.4 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 5: 85 percent / K2CO3 / methanol / 6 h / Ambient temperature 6: 65 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C 7: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h View Scheme
参考文献
Resul, Bahram; Stjernschantz, Johan; No, Kiyo; Liljebris, Charlotta; Selen, Goeran; et al.
Journal of Medicinal Chemistry, 1993 , vol. 36, # 2 p. 243 - 248
反应条件
1: DCC, phosphoric acid / 1,2-dimethoxy-ethane / a) 18 deg C, 30 min, b) RT, 2 h 2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h 3: 33.1 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C 4: 65 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 5: 83.6 percent / K2CO3 / methanol / 6 h / Ambient temperature 6: 83 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C View Scheme
参考文献
Resul, Bahram; Stjernschantz, Johan; No, Kiyo; Liljebris, Charlotta; Selen, Goeran; et al.
Journal of Medicinal Chemistry, 1993 , vol. 36, # 2 p. 243 - 248
反应条件
1: DCC, phosphoric acid / 1,2-dimethoxy-ethane / a) 18 deg C, 30 min, b) RT, 2 h 2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h 3: 52 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C 4: 78.4 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 5: 85 percent / K2CO3 / methanol / 6 h / Ambient temperature 6: 65 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C 7: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h 8: 38 percent / DBU / acetone / 4 h / Ambient temperature View Scheme
参考文献
Resul, Bahram; Stjernschantz, Johan; No, Kiyo; Liljebris, Charlotta; Selen, Goeran; et al.
Journal of Medicinal Chemistry, 1993 , vol. 36, # 2 p. 243 - 248
反应条件
potassium carbonate in methanol; dichloromethane 3 h; Ambient temperature;
参考文献
Zak, Bohumil; Vesely, Ivan; Neumitka, Karel; Palecek, Jaroslav
Collection of Czechoslovak Chemical Communications, 1991 , vol. 56, # 8 p. 1690 - 1700
反应条件
1: 94 percent / imidazole / dimethylformamide / 1 h / Ambient temperature 2: 65 percent / CH3ONa / methanol / 1.33 h / Ambient temperature 3: 90 percent / PPTS / 1,2-dichloro-ethane / 2 h / Ambient temperature View Scheme
参考文献
Terinek, Miroslav; Kozmik, Vaclav; Palecek, Jaroslav
Collection of Czechoslovak Chemical Communications, 1997 , vol. 62, # 8 p. 1325 - 1341
反应条件
1: DCC, phosphoric acid / 1,2-dimethoxy-ethane / a) 18 deg C, 30 min, b) RT, 2 h 2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h 3: 33.1 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C 4: 65 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 5: 83.6 percent / K2CO3 / methanol / 6 h / Ambient temperature View Scheme
参考文献
Resul, Bahram; Stjernschantz, Johan; No, Kiyo; Liljebris, Charlotta; Selen, Goeran; et al.
Journal of Medicinal Chemistry, 1993 , vol. 36, # 2 p. 243 - 248