12(S)-HYDROXY-(5Z,8Z,10E,14Z)-EICOSATETRAENOIC ACID合成路线 （共 60 条）
反应条件
1: 1.) n-Bu3SnLi, 2.) I2 / 2.) Et2O 3: n-PrNH2 / Pd(PPh3)4, CuI 4: 1.) (Sia)2BH, AcOH; 2.) H2O2, NaOH / 1.) THF 5: n-Bu4NF 6: 79 percent / LiOH View Scheme
参考文献
Chemistry Letters, , p. 1785 - 1788
反应条件
2: n-PrNH2 / Pd(PPh3)4, CuI 3: 1.) (Sia)2BH, AcOH; 2.) H2O2, NaOH / 1.) THF 4: n-Bu4NF 5: 79 percent / LiOH View Scheme
参考文献
Chemistry Letters, , p. 1785 - 1788
反应条件
1: n-PrNH2 / Pd(PPh3)4, CuI 2: 1.) (Sia)2BH, AcOH; 2.) H2O2, NaOH / 1.) THF 3: n-Bu4NF 4: 79 percent / LiOH View Scheme
参考文献
Chemistry Letters, , p. 1785 - 1788
反应条件
1: 88 percent / NEt3 / CH2Cl2 / 0.33 h / 0 °C 2: 99 percent / imidazole / dimethylformamide / 23 h / 0 °C 3: 96 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.75 h / -80 °C 4: 71 percent / CrO3, pyridine / CH2Cl2 / 0.33 h / 10 °C 5: 87 percent / NEt3 / CH2Cl2 / 48 h / Ambient temperature 6: 1. n-butyllithium / 1. -20 deg C, THF, hexane 2. a. -80 deg C, b. warm up to -10 deg C, 75 min c. 90 min, -10 deg C 7: 68 percent / aq. oxalic acid / tetrahydrofuran / 1 h / Ambient temperature 8: 86 percent / K2CO3 / 1 h / 23 °C 9: 13.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C 10: aq. NaOH / methanol / 5 h / Ambient temperature View Scheme
参考文献
Bulletin de la Societe Chimique de France, , # 2 p. 298 - 315
反应条件
1: 100 percent / 1N aq. HCl / methanol / 20 h / 0 °C 2: 88 percent / NEt3 / CH2Cl2 / 0.33 h / 0 °C 3: 99 percent / imidazole / dimethylformamide / 23 h / 0 °C 4: 96 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.75 h / -80 °C 5: 71 percent / CrO3, pyridine / CH2Cl2 / 0.33 h / 10 °C 6: 87 percent / NEt3 / CH2Cl2 / 48 h / Ambient temperature 7: 1. n-butyllithium / 1. -20 deg C, THF, hexane 2. a. -80 deg C, b. warm up to -10 deg C, 75 min c. 90 min, -10 deg C 8: 68 percent / aq. oxalic acid / tetrahydrofuran / 1 h / Ambient temperature 9: 86 percent / K2CO3 / 1 h / 23 °C 10: 13.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C 11: aq. NaOH / methanol / 5 h / Ambient temperature View Scheme
参考文献
Bulletin de la Societe Chimique de France, , # 2 p. 298 - 315
反应条件
1: 73 percent / NEt3 / diethyl ether / 0 °C 2: 86 percent / NaI, K2CO3 / acetone / 168 h / 35 °C 3: 76 percent / K2CO3 / acetonitrile / 72 h / 45 °C 4: 1. n-butyllithium / 1. -20 deg C, THF, hexane 2. a. -80 deg C, b. warm up to -10 deg C, 75 min c. 90 min, -10 deg C 5: 68 percent / aq. oxalic acid / tetrahydrofuran / 1 h / Ambient temperature 6: 86 percent / K2CO3 / 1 h / 23 °C 7: 13.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C 8: aq. NaOH / methanol / 5 h / Ambient temperature View Scheme
参考文献
Bulletin de la Societe Chimique de France, , # 2 p. 298 - 315
反应条件
1: 76 percent / K2CO3 / acetonitrile / 72 h / 45 °C 2: 1. n-butyllithium / 1. -20 deg C, THF, hexane 2. a. -80 deg C, b. warm up to -10 deg C, 75 min c. 90 min, -10 deg C 3: 68 percent / aq. oxalic acid / tetrahydrofuran / 1 h / Ambient temperature 4: 86 percent / K2CO3 / 1 h / 23 °C 5: 13.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C 6: aq. NaOH / methanol / 5 h / Ambient temperature View Scheme
参考文献
Bulletin de la Societe Chimique de France, , # 2 p. 298 - 315
反应条件
1: 99 percent / imidazole / dimethylformamide / 23 h / 0 °C 2: 96 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.75 h / -80 °C 3: 71 percent / CrO3, pyridine / CH2Cl2 / 0.33 h / 10 °C 4: 87 percent / NEt3 / CH2Cl2 / 48 h / Ambient temperature 5: 1. n-butyllithium / 1. -20 deg C, THF, hexane 2. a. -80 deg C, b. warm up to -10 deg C, 75 min c. 90 min, -10 deg C 6: 68 percent / aq. oxalic acid / tetrahydrofuran / 1 h / Ambient temperature 7: 86 percent / K2CO3 / 1 h / 23 °C 8: 13.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C 9: aq. NaOH / methanol / 5 h / Ambient temperature View Scheme
参考文献
Bulletin de la Societe Chimique de France, , # 2 p. 298 - 315
反应条件
1: 71 percent / CrO3, pyridine / CH2Cl2 / 0.33 h / 10 °C 2: 87 percent / NEt3 / CH2Cl2 / 48 h / Ambient temperature 3: 1. n-butyllithium / 1. -20 deg C, THF, hexane 2. a. -80 deg C, b. warm up to -10 deg C, 75 min c. 90 min, -10 deg C 4: 68 percent / aq. oxalic acid / tetrahydrofuran / 1 h / Ambient temperature 5: 86 percent / K2CO3 / 1 h / 23 °C 6: 13.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C 7: aq. NaOH / methanol / 5 h / Ambient temperature View Scheme
参考文献
Bulletin de la Societe Chimique de France, , # 2 p. 298 - 315
反应条件
1: 86 percent / NaI, K2CO3 / acetone / 168 h / 35 °C 2: 76 percent / K2CO3 / acetonitrile / 72 h / 45 °C 3: 1. n-butyllithium / 1. -20 deg C, THF, hexane 2. a. -80 deg C, b. warm up to -10 deg C, 75 min c. 90 min, -10 deg C 4: 68 percent / aq. oxalic acid / tetrahydrofuran / 1 h / Ambient temperature 5: 86 percent / K2CO3 / 1 h / 23 °C 6: 13.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C 7: aq. NaOH / methanol / 5 h / Ambient temperature View Scheme
参考文献
Bulletin de la Societe Chimique de France, , # 2 p. 298 - 315
