(2'R)-N-苯甲酰基-2'-脱氧-2'-氟-2'-甲基胞苷 3',5'-二苯甲酸酯合成路线 （共 18 条）
反应条件
1: sodium hypochlorite; TEMPO / 0 °C
2: 78.3 percent / diethyl ether / -78 °C
3: 19.3 percent / (diethylamino)sulfur trifluoride / CH2Cl2 / 20 °C
4: cyclohexene / palladium on carbon / ethanol; ethyl acetate / Heating
5: 0.350 g / pyridine / 20 °C
6: 52.1 percent / formic acid / H2O / 48 h / 60 - 70 °C
7: 88.7 percent / triethylamine / CH2Cl2 / 20 °C
8: 37 percent / tin(IV) chloride / acetonitrile / 4 h / 50 - 55 °C
View Scheme
参考文献
Clark, Jeremy L.; Mason, J. Christian; Hobbs, Ann J.; Hollecker, Laurent; Schinazi, Raymond F.
Journal of Carbohydrate Chemistry, 2006 , vol. 25, # 6 p. 461 - 470
反应条件
1.1: 2,2,2-trifluoroethanol; sodium bis(2-methoxyethoxy)aluminium dihydride / toluene; acetic acid n-butyl ester / -20 - -15 °C
1.2: -20 - 20 °C
2.1: tin(IV) chloride / dichloromethane / 20 h / 30 - 80 °C / 1875.19 Torr / |Sealed tube
2.2: 18 - 25 °C
View Scheme
参考文献
F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CARR, Robert; HILDBRAND, Stefan; HODGES, Mark L.; KAMMERER, Michael; LANG, John F.; LAWRIMORE III, William J.; NGUYEN, Dieu
Patent: WO2013/178571 A1, 2013 ;
反应条件
1: 52.1 percent / formic acid / H2O / 48 h / 60 - 70 °C
2: 88.7 percent / triethylamine / CH2Cl2 / 20 °C
3: 37 percent / tin(IV) chloride / acetonitrile / 4 h / 50 - 55 °C
View Scheme
参考文献
Clark, Jeremy L.; Mason, J. Christian; Hobbs, Ann J.; Hollecker, Laurent; Schinazi, Raymond F.
Journal of Carbohydrate Chemistry, 2006 , vol. 25, # 6 p. 461 - 470
反应条件
1.1: N,N-dimethyl-formamide / 20 h / 20 °C
2.1: pyridine / 20 °C
3.1: dimethyl sulfoxide; trifluoroacetic anhydride / tetrahydrofuran / 2.75 h / -20 - -15 °C
3.2: 0.33 h
4.1: diethyl ether / 2 h / -78 °C / |Inert atmosphere
4.2: 0.75 h / 20 °C
5.1: pyridine / 1.67 h / 0 °C / |Inert atmosphere
6.1: diethylamino-sulfur trifluoride / 1 h / -20 °C / |Inert atmosphere
View Scheme
参考文献
GILEAD SCIENCES, INC.; Delaney, William E.; Link, John O.; Mo, Hongmei; Oldach, David W.; Ray, Adrian S.; Watkins, William J.; Yang, Cheng Yong; Zhong, Weidong
Patent: US2013/273005 A1, 2013 ;
反应条件
1.1: N,N-dimethyl-formamide / 20 h / 20 °C
2.1: pyridine / 20 °C
3.1: dimethyl sulfoxide; trifluoroacetic anhydride / tetrahydrofuran / 2.75 h / -20 - -15 °C
3.2: 0.33 h
4.1: diethyl ether / 2 h / -78 °C / |Inert atmosphere
4.2: 0.75 h / 20 °C
5.1: pyridine / 1.67 h / 0 °C / |Inert atmosphere
6.1: diethylamino-sulfur trifluoride / 1 h / -20 °C / |Inert atmosphere
View Scheme
参考文献
GILEAD SCIENCES, INC.; Delaney, William E.; Link, John O.; Mo, Hongmei; Oldach, David W.; Ray, Adrian S.; Watkins, William J.; Yang, Cheng Yong; Zhong, Weidong
Patent: US2013/273005 A1, 2013 ;
反应条件
1.1: pyridine / 20 °C
2.1: dimethyl sulfoxide; trifluoroacetic anhydride / tetrahydrofuran / 2.75 h / -20 - -15 °C
2.2: 0.33 h
3.1: diethyl ether / 2 h / -78 °C / |Inert atmosphere
3.2: 0.75 h / 20 °C
4.1: pyridine / 1.67 h / 0 °C / |Inert atmosphere
5.1: diethylamino-sulfur trifluoride / 1 h / -20 °C / |Inert atmosphere
View Scheme
参考文献
GILEAD SCIENCES, INC.; Delaney, William E.; Link, John O.; Mo, Hongmei; Oldach, David W.; Ray, Adrian S.; Watkins, William J.; Yang, Cheng Yong; Zhong, Weidong
Patent: US2013/273005 A1, 2013 ;
反应条件
1.1: ammonium sulfate / isopropanol acetate / 0.5 h / 88 - 90 °C
2.1: tin(IV) chloride / dichloromethane / 20 h / 75 - 80 °C / 1875.19 Torr
2.2: 18 - 25 °C
View Scheme
参考文献
Carr, Robert; Hildbrand, Stefan; Hodges, Mark L.; Kammerer, Michael; Lang, John F.; Lawrimore, III, William J.; Nguyen, Dieu
Patent: US2013/324709 A1, 2013 ;
反应条件
1: pyridine / 1.67 h / 0 °C / |Inert atmosphere
2: diethylamino-sulfur trifluoride / 1 h / -20 °C / |Inert atmosphere
View Scheme
参考文献
GILEAD SCIENCES, INC.; Delaney, William E.; Link, John O.; Mo, Hongmei; Oldach, David W.; Ray, Adrian S.; Watkins, William J.; Yang, Cheng Yong; Zhong, Weidong
Patent: US2013/273005 A1, 2013 ;
