反式-4-羟基-L-脯氨酸甲酯盐酸盐合成路线 （共 70 条）
反应条件
1: 92 percent / aq. sodium bicarbonate / tetrahydrofuran / 2 h 2: 93 percent / imidazole / dimethylformamide / 2 h / 20 °C 3: 97 percent / lithium chloride; sodium borohydride / tetrahydrofuran; methanol / 12 h / 20 °C View Scheme
参考文献
Fransson, Rebecca; McCracken, Alison N.; Chen, Bin; McMonigle, Ryan J.; Edinger, Aimee L.; Hanessian, Stephen
ACS Medicinal Chemistry Letters, 2013 , vol. 4, # 10 p. 969 - 973
反应条件
1: 53.4 g / triethylamine / CH2Cl2 / 4 h / 0 - 5 °C 2: 56.2 g / triethylamine / CH2Cl2 / 3 h / 0 - 5 °C 3: 88.7 percent / dimethylsulfoxide / 90 °C View Scheme
参考文献
Rawson, David J.; Brugier, Delphine; Harrison, Anthony; Hough, Jo; Newman, Julie; Otterburn, Joe; Maw, Graham N.; Price, Jenny; Thompson, Lisa R.; Turnpenny, Paul; Warren, Andrew N.
Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 12 p. 3767 - 3770
反应条件
1.1: triethylamine
2.1: sodium periodate; ruthenium trichloride
4.1: diethylzinc; trifluoroacetic acid / hexane; dichloromethane / 1 h / -5 °C / Inert atmosphere
4.2: 72 h / -5 - 30 °C / Inert atmosphere
4.3: 24 h / 20 °C
View Scheme
参考文献
Tymtsunik, Andriy V.; Bilenko, Vitaliy A.; Ivon, Yevhen M.; Grygorenko, Oleksandr O.; Komarov, Igor V.
Tetrahedron Letters, 2012 , vol. 53, # 30 p. 3847 - 3849
反应条件
1.1: triethylamine
2.1: sodium periodate; ruthenium trichloride
4.1: diethylzinc; trifluoroacetic acid / hexane; dichloromethane / 1 h / -5 °C / Inert atmosphere
4.2: 72 h / -5 - 30 °C / Inert atmosphere
View Scheme
参考文献
Tymtsunik, Andriy V.; Bilenko, Vitaliy A.; Ivon, Yevhen M.; Grygorenko, Oleksandr O.; Komarov, Igor V.
Tetrahedron Letters, 2012 , vol. 53, # 30 p. 3847 - 3849
反应条件
1: 100 percent / aq. NaOH / tetrahydrofuran / 20 °C
2: trichloroisocyanuric acid; TEMPO / CH2Cl2
3: HMPT; Zn / tetrahydrofuran
4: TFA / CH2Cl2
View Scheme
参考文献
Kamal, Ahmed; Reddy; Reddy, D. Rajasekhar; Laxman; Murthy
Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 22 p. 5699 - 5702
反应条件
1: 76 percent / Et3N / CHCl3 / 0 °C
2: 1.) PPh3, DEAD, PhCO2H; 2.) KOH / 1.) toluene; 2.) MeOH
3: HCO2H / 1,2-dichloro-ethane
View Scheme
参考文献
Demange, Luc; Menez, Andre; Dugave, Christophe
Tetrahedron Letters, 1998 , vol. 39, # 10 p. 1169 - 1172
反应条件
1: 91 percent / Et3N / CH2Cl2 / 8 h / Ambient temperature
2: 93.8 percent / Ph3P, DEAD, CH3I / tetrahydrofuran / 10 h / Ambient temperature
View Scheme
参考文献
Schumacher, Kelly K.; Jiang, Jianjun; Joullie, Madeleine M.
Tetrahedron Asymmetry, 1998 , vol. 9, # 1 p. 47 - 53
反应条件
1: triethylamine
2: sodium periodate; ruthenium trichloride
View Scheme
参考文献
Tymtsunik, Andriy V.; Bilenko, Vitaliy A.; Ivon, Yevhen M.; Grygorenko, Oleksandr O.; Komarov, Igor V.
Tetrahedron Letters, 2012 , vol. 53, # 30 p. 3847 - 3849
反应条件
1.1: triethylamine / dichloromethane / 17 h / 0 °C
2.1: lithium borohydride / tetrahydrofuran / 26 h / 0 - 20 °C
3.1: pyridine / dichloromethane / 18 h / 40 °C
4.1: trimethylsilylazide; tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 70 °C
5.1: triethylamine / dichloromethane / 0.5 h / 0 °C
6.1: triphenylphosphine / tetrahydrofuran / 2 h / 20 °C
6.2: 18 h
7.1: 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
反应条件
1: 95 percent / Et3N / CH2Cl2 / Ambient temperature
2: 81 percent / PDC, 3 Angstroem molecular sieves / CH2Cl2 / Ambient temperature
3: 89 percent / DAST / CH2Cl2 / -78 deg C to r.t.
4: 95 percent / LiOH / acetonitrile; H2O / Ambient temperature
5: TFA / CH2Cl2
View Scheme
参考文献
Demange, Luc; Menez, Andre; Dugave, Christophe
Tetrahedron Letters, 1998 , vol. 39, # 10 p. 1169 - 1172
