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: 86 percent / BuLi / tetrahydrofuran / 18 h / Heating
2: 1.) dicyclohexylborane, 2.) AcOH / 1.) THF, r.t., 2 h, 2.) THF, r.t., 1 h
3: Br2 / CH2Cl2 / 0.17 h / -78 °C
4: NaOMe / methanol / 1.) 0 deg C, 1 h, 2.) r.t., 2 h
6: 43 percent / n-BuLi / tetrahydrofuran; hexane / 24 h / Ambient temperature
7: 51 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C, 1 h
8: LiAlH4 / diethyl ether / 3 h / 0 °C
9: imidazole / dimethylformamide / 1 h / Ambient temperature
10: 1.) 9-BBN, 2.) NaOH, H2O2 / 1.) reflux, 24 h
11: 91 percent / TfOH / cyclohexane; CH2Cl2 / 0.5 h / Ambient temperature
12: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature
13: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature
14: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C
15: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature
16: benzenesulfonyl chloride, pyridine / 15 h / 0 °C
17: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
18: 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: LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C, 1 h
2: LiAlH4 / diethyl ether / 3 h / 0 °C
3: imidazole / dimethylformamide / 1 h / Ambient temperature
4: 1.) 9-BBN, 2.) NaOH, H2O2 / 1.) reflux, 24 h
5: 91 percent / TfOH / cyclohexane; CH2Cl2 / 0.5 h / Ambient temperature
6: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature
7: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature
8: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C
9: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature
10: benzenesulfonyl chloride, pyridine / 15 h / 0 °C
11: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
12: 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: 86 percent / potassium hydroxide / tetrahydrofuran; H2O / 22 h / Heating
2.1: oxalyl chloride; dimethylformamide / CH2Cl2 / 0.83 h / 20 °C
3.1: 4.41 g / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / 20 °C
4.1: 61 percent / AD-mix-α; methanesulfonamide; sodium hydrogen carbonate / 2-methyl-propan-2-ol; H2O / 25 h / 0 °C
5.1: 92 percent / thionyl chloride / CCl4 / 22 h / Heating
6.1: copper(I) cyanide / tetrahydrofuran; hexane / 0.25 h / 20 °C
6.2: 84 percent / boron trifluoride diethyl etherate / tetrahydrofuran; hexane / 1 h / -78 °C
7.1: 74 percent / acetic acid; zinc / 4 h / 20 °C
8.1: sodium hydrogen carbonate; bromine / methanol; CCl4; H2O / 0.01 h / 20 °C
8.2: 63 percent / di-tert-butyl peroxyoxalate; diphenyl diselenide; tributyltin hydride / toluene / 2.5 h / 0 °C
9.1: 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: Br2 / CH2Cl2 / 0.17 h / -78 °C
2: NaOMe / methanol / 1.) 0 deg C, 1 h, 2.) r.t., 2 h
4: 43 percent / n-BuLi / tetrahydrofuran; hexane / 24 h / Ambient temperature
5: 51 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C, 1 h
6: LiAlH4 / diethyl ether / 3 h / 0 °C
7: imidazole / dimethylformamide / 1 h / Ambient temperature
8: 1.) 9-BBN, 2.) NaOH, H2O2 / 1.) reflux, 24 h
9: 91 percent / TfOH / cyclohexane; CH2Cl2 / 0.5 h / Ambient temperature
10: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature
11: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature
12: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C
13: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature
14: benzenesulfonyl chloride, pyridine / 15 h / 0 °C
15: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
16: 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: imidazole / dimethylformamide / 1 h / Ambient temperature
2: 1.) 9-BBN, 2.) NaOH, H2O2 / 1.) reflux, 24 h
3: 91 percent / TfOH / cyclohexane; CH2Cl2 / 0.5 h / Ambient temperature
4: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature
5: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature
6: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C
7: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature
8: benzenesulfonyl chloride, pyridine / 15 h / 0 °C
9: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
10: 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: benzenesulfonyl chloride, pyridine / 15 h / 0 °C
2: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
3: 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: LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C, 1 h
2: LiAlH4 / diethyl ether / 3 h / 0 °C
3: imidazole / dimethylformamide / 1 h / Ambient temperature
4: 1.) 9-BBN, 2.) NaOH, H2O2 / 1.) reflux, 24 h
5: 91 percent / TfOH / cyclohexane; CH2Cl2 / 0.5 h / Ambient temperature
6: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature
7: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature
8: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C
9: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature
10: benzenesulfonyl chloride, pyridine / 15 h / 0 °C
11: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
12: 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: 91 percent / TfOH / cyclohexane; CH2Cl2 / 0.5 h / Ambient temperature
2: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature
3: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature
4: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C
5: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature
6: benzenesulfonyl chloride, pyridine / 15 h / 0 °C
7: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
8: 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: 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
