N-去甲酰基-N-苄氧羰基奥利司他合成路线 （共 43 条）
反应条件
1: LiAlH4 / diethyl ether / 3 h / 0 °C
2: imidazole / dimethylformamide / 1 h / Ambient temperature
3: 1.) 9-BBN, 2.) NaOH, H2O2 / 1.) reflux, 24 h
4: 91 percent / TfOH / cyclohexane; CH2Cl2 / 0.5 h / Ambient temperature
5: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature
6: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature
7: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C
8: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature
9: benzenesulfonyl chloride, pyridine / 15 h / 0 °C
10: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
11: DCC, DMAP / CH2Cl2; dimethylformamide / 1 h / Ambient temperature
View Scheme
参考文献
Fleming, Ian; Lawrence, Nicholas J.
Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 17 p. 2679 - 2686
反应条件
1: 1.) 9-BBN, 2.) NaOH, H2O2 / 1.) reflux, 24 h
2: 91 percent / TfOH / cyclohexane; CH2Cl2 / 0.5 h / Ambient temperature
3: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature
4: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature
5: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C
6: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature
7: benzenesulfonyl chloride, pyridine / 15 h / 0 °C
8: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
9: DCC, DMAP / CH2Cl2; dimethylformamide / 1 h / Ambient temperature
View Scheme
参考文献
Fleming, Ian; Lawrence, Nicholas J.
Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 17 p. 2679 - 2686
反应条件
1.1: oxalyl chloride; dimethylformamide / CH2Cl2 / 0.83 h / 20 °C
2.1: 4.41 g / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / 20 °C
3.1: 61 percent / AD-mix-α; methanesulfonamide; sodium hydrogen carbonate / 2-methyl-propan-2-ol; H2O / 25 h / 0 °C
4.1: 92 percent / thionyl chloride / CCl4 / 22 h / Heating
5.1: copper(I) cyanide / tetrahydrofuran; hexane / 0.25 h / 20 °C
5.2: 84 percent / boron trifluoride diethyl etherate / tetrahydrofuran; hexane / 1 h / -78 °C
6.1: 74 percent / acetic acid; zinc / 4 h / 20 °C
7.1: sodium hydrogen carbonate; bromine / methanol; CCl4; H2O / 0.01 h / 20 °C
7.2: 63 percent / di-tert-butyl peroxyoxalate; diphenyl diselenide; tributyltin hydride / toluene / 2.5 h / 0 °C
8.1: 87 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / dimethylformamide / 1.33 h / 20 °C
View Scheme
参考文献
Bodkin, Jennifer A.; Humphries, Edward J.; McLeod, Malcolm D.
Australian Journal of Chemistry, 2003 , vol. 56, # 8 p. 795 - 803
反应条件
1.1: 61 percent / AD-mix-α; methanesulfonamide; sodium hydrogen carbonate / 2-methyl-propan-2-ol; H2O / 25 h / 0 °C
2.1: 92 percent / thionyl chloride / CCl4 / 22 h / Heating
3.1: copper(I) cyanide / tetrahydrofuran; hexane / 0.25 h / 20 °C
3.2: 84 percent / boron trifluoride diethyl etherate / tetrahydrofuran; hexane / 1 h / -78 °C
4.1: 74 percent / acetic acid; zinc / 4 h / 20 °C
5.1: sodium hydrogen carbonate; bromine / methanol; CCl4; H2O / 0.01 h / 20 °C
5.2: 63 percent / di-tert-butyl peroxyoxalate; diphenyl diselenide; tributyltin hydride / toluene / 2.5 h / 0 °C
6.1: 87 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / dimethylformamide / 1.33 h / 20 °C
View Scheme
参考文献
Bodkin, Jennifer A.; Humphries, Edward J.; McLeod, Malcolm D.
Australian Journal of Chemistry, 2003 , vol. 56, # 8 p. 795 - 803
反应条件
1.1: 92 percent / thionyl chloride / CCl4 / 22 h / Heating
2.1: copper(I) cyanide / tetrahydrofuran; hexane / 0.25 h / 20 °C
2.2: 84 percent / boron trifluoride diethyl etherate / tetrahydrofuran; hexane / 1 h / -78 °C
3.1: 74 percent / acetic acid; zinc / 4 h / 20 °C
4.1: sodium hydrogen carbonate; bromine / methanol; CCl4; H2O / 0.01 h / 20 °C
4.2: 63 percent / di-tert-butyl peroxyoxalate; diphenyl diselenide; tributyltin hydride / toluene / 2.5 h / 0 °C
5.1: 87 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / dimethylformamide / 1.33 h / 20 °C
View Scheme
参考文献
Bodkin, Jennifer A.; Humphries, Edward J.; McLeod, Malcolm D.
Australian Journal of Chemistry, 2003 , vol. 56, # 8 p. 795 - 803
反应条件
1.1: copper(I) cyanide / tetrahydrofuran; hexane / 0.25 h / 20 °C
1.2: 84 percent / boron trifluoride diethyl etherate / tetrahydrofuran; hexane / 1 h / -78 °C
2.1: 74 percent / acetic acid; zinc / 4 h / 20 °C
3.1: sodium hydrogen carbonate; bromine / methanol; CCl4; H2O / 0.01 h / 20 °C
3.2: 63 percent / di-tert-butyl peroxyoxalate; diphenyl diselenide; tributyltin hydride / toluene / 2.5 h / 0 °C
4.1: 87 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / dimethylformamide / 1.33 h / 20 °C
View Scheme
参考文献
Bodkin, Jennifer A.; Humphries, Edward J.; McLeod, Malcolm D.
Australian Journal of Chemistry, 2003 , vol. 56, # 8 p. 795 - 803
反应条件
1.1: sodium hydrogen carbonate; bromine / methanol; CCl4; H2O / 0.01 h / 20 °C
1.2: 63 percent / di-tert-butyl peroxyoxalate; diphenyl diselenide; tributyltin hydride / toluene / 2.5 h / 0 °C
2.1: 87 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / dimethylformamide / 1.33 h / 20 °C
View Scheme
参考文献
Bodkin, Jennifer A.; Humphries, Edward J.; McLeod, Malcolm D.
Australian Journal of Chemistry, 2003 , vol. 56, # 8 p. 795 - 803
反应条件
1.1: 74 percent / acetic acid; zinc / 4 h / 20 °C
2.1: sodium hydrogen carbonate; bromine / methanol; CCl4; H2O / 0.01 h / 20 °C
2.2: 63 percent / di-tert-butyl peroxyoxalate; diphenyl diselenide; tributyltin hydride / toluene / 2.5 h / 0 °C
3.1: 87 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / dimethylformamide / 1.33 h / 20 °C
View Scheme
参考文献
Bodkin, Jennifer A.; Humphries, Edward J.; McLeod, Malcolm D.
Australian Journal of Chemistry, 2003 , vol. 56, # 8 p. 795 - 803
反应条件
1.1: 68 percent / molecular sieves 4 Angstroem; lithium hydroxide / tetrahydrofuran / 40 h / Heating
2.1: 86 percent / potassium hydroxide / tetrahydrofuran; H2O / 22 h / Heating
3.1: oxalyl chloride; dimethylformamide / CH2Cl2 / 0.83 h / 20 °C
4.1: 4.41 g / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / 20 °C
5.1: 61 percent / AD-mix-α; methanesulfonamide; sodium hydrogen carbonate / 2-methyl-propan-2-ol; H2O / 25 h / 0 °C
6.1: 92 percent / thionyl chloride / CCl4 / 22 h / Heating
7.1: copper(I) cyanide / tetrahydrofuran; hexane / 0.25 h / 20 °C
7.2: 84 percent / boron trifluoride diethyl etherate / tetrahydrofuran; hexane / 1 h / -78 °C
8.1: 74 percent / acetic acid; zinc / 4 h / 20 °C
9.1: sodium hydrogen carbonate; bromine / methanol; CCl4; H2O / 0.01 h / 20 °C
9.2: 63 percent / di-tert-butyl peroxyoxalate; diphenyl diselenide; tributyltin hydride / toluene / 2.5 h / 0 °C
10.1: 87 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / dimethylformamide / 1.33 h / 20 °C
View Scheme
参考文献
Bodkin, Jennifer A.; Humphries, Edward J.; McLeod, Malcolm D.
Australian Journal of Chemistry, 2003 , vol. 56, # 8 p. 795 - 803
反应条件
1.1: 4.41 g / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / 20 °C
2.1: 61 percent / AD-mix-α; methanesulfonamide; sodium hydrogen carbonate / 2-methyl-propan-2-ol; H2O / 25 h / 0 °C
3.1: 92 percent / thionyl chloride / CCl4 / 22 h / Heating
4.1: copper(I) cyanide / tetrahydrofuran; hexane / 0.25 h / 20 °C
4.2: 84 percent / boron trifluoride diethyl etherate / tetrahydrofuran; hexane / 1 h / -78 °C
5.1: 74 percent / acetic acid; zinc / 4 h / 20 °C
6.1: sodium hydrogen carbonate; bromine / methanol; CCl4; H2O / 0.01 h / 20 °C
6.2: 63 percent / di-tert-butyl peroxyoxalate; diphenyl diselenide; tributyltin hydride / toluene / 2.5 h / 0 °C
7.1: 87 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / dimethylformamide / 1.33 h / 20 °C
View Scheme
参考文献
Bodkin, Jennifer A.; Humphries, Edward J.; McLeod, Malcolm D.
Australian Journal of Chemistry, 2003 , vol. 56, # 8 p. 795 - 803
