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: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature
2: benzenesulfonyl chloride, pyridine / 15 h / 0 °C
3: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
4: 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: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature
2: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature
3: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C
4: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature
5: benzenesulfonyl chloride, pyridine / 15 h / 0 °C
6: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
7: 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: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
2: 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.) dicyclohexylborane, 2.) AcOH / 1.) THF, r.t., 2 h, 2.) THF, r.t., 1 h
2: Br2 / CH2Cl2 / 0.17 h / -78 °C
3: NaOMe / methanol / 1.) 0 deg C, 1 h, 2.) r.t., 2 h
5: 43 percent / n-BuLi / tetrahydrofuran; hexane / 24 h / Ambient temperature
6: 51 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C, 1 h
7: LiAlH4 / diethyl ether / 3 h / 0 °C
8: imidazole / dimethylformamide / 1 h / Ambient temperature
9: 1.) 9-BBN, 2.) NaOH, H2O2 / 1.) reflux, 24 h
10: 91 percent / TfOH / cyclohexane; CH2Cl2 / 0.5 h / Ambient temperature
11: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature
12: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature
13: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C
14: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature
15: benzenesulfonyl chloride, pyridine / 15 h / 0 °C
16: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
17: 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: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature
2: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C
3: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature
4: benzenesulfonyl chloride, pyridine / 15 h / 0 °C
5: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
6: 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: 43 percent / n-BuLi / tetrahydrofuran; hexane / 24 h / Ambient temperature
2: 51 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C, 1 h
3: LiAlH4 / diethyl ether / 3 h / 0 °C
4: imidazole / dimethylformamide / 1 h / Ambient temperature
5: 1.) 9-BBN, 2.) NaOH, H2O2 / 1.) reflux, 24 h
6: 91 percent / TfOH / cyclohexane; CH2Cl2 / 0.5 h / Ambient temperature
7: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature
8: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature
9: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C
10: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature
11: benzenesulfonyl chloride, pyridine / 15 h / 0 °C
12: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
13: 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
2: 43 percent / n-BuLi / tetrahydrofuran; hexane / 24 h / Ambient temperature
3: 51 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C, 1 h
4: LiAlH4 / diethyl ether / 3 h / 0 °C
5: imidazole / dimethylformamide / 1 h / Ambient temperature
6: 1.) 9-BBN, 2.) NaOH, H2O2 / 1.) reflux, 24 h
7: 91 percent / TfOH / cyclohexane; CH2Cl2 / 0.5 h / Ambient temperature
8: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature
9: 88 percent / PDC / dimethylformamide / 2 h / Ambient temperature
10: 62 percent / Jones' reagent / acetone / 0.75 h / 0 °C
11: 38 percent / Hg(OAc)2, AcOOH, AcOH / 3 h / Ambient temperature
12: benzenesulfonyl chloride, pyridine / 15 h / 0 °C
13: 92 percent / H2 / 10percent Pd/C / tetrahydrofuran / 15 h
14: 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: 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: 51 percent / 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: 29 percent / 9-BBN / 3 h / Heating
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
