(3S,4s)-4-氨基-3-羟基-5-苯基戊酸合成路线 （共 26 条）
反应条件
1: 76 percent / DIBAL-H / CH2Cl2 / -78 - 20 °C
2: 60 percent / tetrahydrofuran / 0 - 20 °C
3: 90 percent / H2 / Pd/C / ethyl acetate; methanol
4: 67 percent / AcOH / toluene / Heating
5: 73 percent / cc. HCl / 80 °C
View Scheme
参考文献
Kondekar, Nagendra B.; Kandula, Subba Rao V.; Kumar, Pradeep
Tetrahedron Letters, 2004 , vol. 45, # 28 p. 5477 - 5479
反应条件
1: 87 percent / HCl / methanol / Heating
2: Et3N / CH2Cl2 / 0 - 20 °C
3: 89 percent / p-toluenesulfonic acid / CH2Cl2 / 20 °C
4: 76 percent / DIBAL-H / CH2Cl2 / -78 - 20 °C
5: 60 percent / tetrahydrofuran / 0 - 20 °C
6: 90 percent / H2 / Pd/C / ethyl acetate; methanol
7: 67 percent / AcOH / toluene / Heating
8: 73 percent / cc. HCl / 80 °C
View Scheme
参考文献
Kondekar, Nagendra B.; Kandula, Subba Rao V.; Kumar, Pradeep
Tetrahedron Letters, 2004 , vol. 45, # 28 p. 5477 - 5479
反应条件
1: 18 percent / tetrahydrofuran / 1.5 h / 0 °C
2: 81 percent / trifluoroacetic acid / 3 h / 20 °C
3: 99 percent / H2 / 20 percent Pd(OH)2-C / methanol; H2O / 22 h
View Scheme
参考文献
Andres, Jose M; Pedrosa, Rafael; Perez, Alberto; Perez-Encabo, Alfonso
Tetrahedron, 2001 , vol. 57, # 40 p. 8521 - 8530
反应条件
1: 81 percent / trifluoroacetic acid / 3 h / 20 °C
2: 99 percent / H2 / 20 percent Pd(OH)2-C / methanol; H2O / 22 h
View Scheme
参考文献
Andres, Jose M; Pedrosa, Rafael; Perez, Alberto; Perez-Encabo, Alfonso
Tetrahedron, 2001 , vol. 57, # 40 p. 8521 - 8530
反应条件
1.1: carbonyl diimidazole / tetrahydrofuran / 24 h / 20 °C
1.2: 85 percent / tetrahydrofuran / 1 h / -78 °C
2.1: TiCl4 / CH2Cl2 / 0.5 h
2.2: 75 percent / BH3-pyridine complex / tetrahydrofuran / 1 h / -78 °C
3.1: 95 percent / LiOH / tetrahydrofuran; H2O / 24 h
4.1: HCOOH / 6 h / 20 °C
View Scheme
参考文献
Meloni, Marco Massimiliano; Taddei, Maurizio
Organic Letters, 2001 , vol. 3, # 3 p. 337 - 340
反应条件
1.1: TiCl4 / CH2Cl2 / 0.5 h
1.2: 75 percent / BH3-pyridine complex / tetrahydrofuran / 1 h / -78 °C
2.1: 95 percent / LiOH / tetrahydrofuran; H2O / 24 h
3.1: HCOOH / 6 h / 20 °C
View Scheme
参考文献
Meloni, Marco Massimiliano; Taddei, Maurizio
Organic Letters, 2001 , vol. 3, # 3 p. 337 - 340
反应条件
1: NH4Cl, Zn-Co couple / methanol / 2 h / 20 °C
2: 1.) CF3COOH, 2.) aq. HCl (12 N) / 1) 20 deg C, 1.5 h; 2) 80 deg C, 3 h
View Scheme
参考文献
Kanazawa, Alice; Gillet, Sandra; Delair, Philippe; Greene, Andrew E.
Journal of Organic Chemistry, 1998 , vol. 63, # 14 p. 4660 - 4663
反应条件
1: 85 percent / 20 percent aq. NaOH, 30 percent aq. H2O2 / RT, 1 h, reflux, 2 h
2: sodium, liquid ammonia / tetrahydrofuran / 3 h / -78 °C
View Scheme
参考文献
Fuji, Kaoru; Kawabata, Takeo; Kiryu, Yoshimitsu; Sugiura, Yukio
Heterocycles, 1996 , vol. 42, # 2 p. 701 - 722
反应条件
1: NaH / tetrahydrofuran / 0 °C
2: I2 / acetonitrile / Ambient temperature
3: 85 percent / n-Bu3SnH / toluene / Heating
4: alkaline hydrolysis
View Scheme
参考文献
Misiti; Zappia
Tetrahedron Letters, 1990 , vol. 31, # 50 p. 7359 - 7362
反应条件
1: DIBAH / toluene / -78 °C
2: NaH / tetrahydrofuran / 0 °C
3: I2 / acetonitrile / Ambient temperature
4: 85 percent / n-Bu3SnH / toluene / Heating
5: alkaline hydrolysis
View Scheme
参考文献
Misiti; Zappia
Tetrahedron Letters, 1990 , vol. 31, # 50 p. 7359 - 7362
