Boc-反-4-羟基-L-脯氨酸醇合成路线 (共 28 条)
反应条件
1.1: 78 percent / TEA; DMAP / CH2Cl2 2.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 3.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C 4.1: Raney-Ni; hydrogen / methanol / Heating 5.1: TBAF / tetrahydrofuran 6.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme
参考文献
Del Valle, Juan R.; Goodman, Murray
Journal of Organic Chemistry, 2003 , vol. 68, # 10 p. 3923 - 3931
反应条件
1.1: 78 percent / TEA; DMAP / CH2Cl2 2.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 3.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C 3.2: 70 percent / tetrahydrofuran / 20 °C 4.1: 95 percent / Raney-Ni; hydrogen / methanol / 18 h / 20 °C / 760 Torr 5.1: TBAF / tetrahydrofuran / 6 h / 20 °C 5.2: NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme
参考文献
Del Valle, Juan R.; Goodman, Murray
Journal of Organic Chemistry, 2003 , vol. 68, # 10 p. 3923 - 3931
反应条件
1: pyridine / 1.) 0 deg C, 2.) stored in the refrigerator for 5 days 2: 63.5 percent / 1.) Na/NH3 (liq.) / 1.) THF, temperature of liquid NH3, 2.) room temperature, 18.5 h View Scheme
参考文献
Baker, Gregory L.; Fritschel, Scott J.; Stille, John R.; Stille, John K.
Journal of Organic Chemistry, 1981 , vol. 46, # 14 p. 2954 - 2960
反应条件
1: pyridine / 1.) 0 deg C, 2.) stored in the refrigerator for 5 days 2: 63.5 percent / 1.) Na/NH3 (liq.) / 1.) THF, temperature of liquid NH3, 2.) room temperature, 18.5 h 3: CF3COOH / 0.5 h / 0 °C View Scheme
参考文献
Baker, Gregory L.; Fritschel, Scott J.; Stille, John R.; Stille, John K.
Journal of Organic Chemistry, 1981 , vol. 46, # 14 p. 2954 - 2960
反应条件
1.1: pyridine / dichloromethane / 18 h / 40 °C 2.1: trimethylsilylazide; tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 70 °C 3.1: triethylamine / dichloromethane / 0.5 h / 0 °C 4.1: triphenylphosphine / tetrahydrofuran / 2 h / 20 °C 4.2: 18 h View Scheme
参考文献
Beinat, Corinne; Banister, Samuel D.; McErlean, Christopher S.P.; Kassiou, Michael
Tetrahedron Letters, 2013 , vol. 54, # 39 p. 5345 - 5347
反应条件
1.1: 78 percent / TEA; DMAP / CH2Cl2 2.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 3.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C 3.2: 70 percent / tetrahydrofuran / 20 °C 4.1: 81 percent / TBAF / tetrahydrofuran / 6 h / 20 °C 5.1: 93 percent / Ir(COD)PyPCy3PF6; hydrogen / CH2Cl2 / 18 h / 20 °C / 760 Torr 6.1: 86 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme
参考文献
Del Valle, Juan R.; Goodman, Murray
Journal of Organic Chemistry, 2003 , vol. 68, # 10 p. 3923 - 3931
反应条件
1.1: 78 percent / TEA; DMAP / CH2Cl2
2.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C
3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
3.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C
4.1: Raney-Ni; hydrogen / methanol / Heating
5.1: TBAF / tetrahydrofuran
View Scheme
参考文献
Del Valle, Juan R.; Goodman, Murray
Journal of Organic Chemistry, 2003 , vol. 68, # 10 p. 3923 - 3931
反应条件
1.1: pyridine / dichloromethane / 18 h / 40 °C
2.1: trimethylsilylazide; tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 70 °C
3.1: triethylamine / dichloromethane / 0.5 h / 0 °C
4.1: triphenylphosphine / tetrahydrofuran / 2 h / 20 °C
4.2: 18 h
5.1: hydrogenchloride / methanol; 1,4-dioxane / 0.5 h / 20 °C
View Scheme
参考文献
Beinat, Corinne; Banister, Samuel D.; McErlean, Christopher S.P.; Kassiou, Michael
Tetrahedron Letters, 2013 , vol. 54, # 39 p. 5345 - 5347