Cryptophycin 1合成路线 （共 35 条）
反应条件
1: With pyridinium p-toluenesulfonate; trimethyl orthoformate in dichloromethane
T=20°C; 2 h;
2: With acetyl-bromide in dichloromethane
T=20°C; 4 h;
3: With tetrabutylammomium bromide; potassium hydrogencarbonate in ethylene glycol dimethyl ether
T=40°C; 27 h;
参考文献
Mast, Christian Alexander; Eissler, Stefan; Stoncius, Arvydas; Stammler, Hans-Georg; Neumann, Beate; Sewald, Norbert
Chemistry - A European Journal, 2005 , vol. 11, # 16 p. 4667 - 4677
反应条件
potassium carbonate in acetone
T=70°C; 4 h;
参考文献
Golakoti, Trimurtulu; Ogino, Junichi; Heltzel, Carl E.; Le Husebo, Trang; Jensen, Craig M.; Larsen, Linda K.; Patterson, Gregory M. L.; Moore, Richard E.; Mooberry, Susan L.; Corbett, Thomas H.; Valeriote, Frederick A.
Journal of the American Chemical Society, 1995 , vol. 117, # 49 p. 12030 - 12049
反应条件
potassium carbonate in acetone
参考文献
Gardinier, Kevin M.; Leahy, James W.
Journal of Organic Chemistry, 1997 , vol. 62, # 21 p. 7098 - 7099
反应条件
1.1: 99 percent / LiAlH4 / tetrahydrofuran / 5 - 20 °C
2.1: 94 percent / DABCO / CH2Cl2 / 20 °C
3.1: 99 percent / NaHCO3 / dimethylsulfoxide / 5 h / 60 °C
4.1: 92 percent / DIBALH / toluene / 2 h / -78 °C
5.1: NaH / tetrahydrofuran / 0 - 20 °C
5.2: 85 percent / tetrahydrofuran / 3 h / -78 °C
6.1: 97 percent / p-toluenesulfinic acid / [Pd(PPh3)4] / CH2Cl2 / 2 h / 20 °C
7.1: 93 percent / DMAP; EDC; Et3N / CH2Cl2 / 31 h / 0 - 20 °C
8.1: aq. TFA / CH2Cl2 / 0 - 20 °C
9.1: 77 percent / HATU; DIPEA / dimethylformamide / 1.5 h / 0 - 20 °C
10.1: (CH3O)3CH; PPTS / CH2Cl2 / 2 h / 20 °C
10.2: AcBr / CH2Cl2 / 4 h / 20 °C
10.3: 72 percent / KHCO3; (nBu)4NBr / 1,2-dimethoxy-ethane / 27 h / 40 °C
View Scheme
参考文献
Mast, Christian Alexander; Eissler, Stefan; Stoncius, Arvydas; Stammler, Hans-Georg; Neumann, Beate; Sewald, Norbert
Chemistry - A European Journal, 2005 , vol. 11, # 16 p. 4667 - 4677
反应条件
1.1: 97 percent / p-toluenesulfinic acid / [Pd(PPh3)4] / CH2Cl2 / 2 h / 20 °C
2.1: 93 percent / DMAP; EDC; Et3N / CH2Cl2 / 31 h / 0 - 20 °C
3.1: aq. TFA / CH2Cl2 / 0 - 20 °C
4.1: 77 percent / HATU; DIPEA / dimethylformamide / 1.5 h / 0 - 20 °C
5.1: (CH3O)3CH; PPTS / CH2Cl2 / 2 h / 20 °C
5.2: AcBr / CH2Cl2 / 4 h / 20 °C
5.3: 72 percent / KHCO3; (nBu)4NBr / 1,2-dimethoxy-ethane / 27 h / 40 °C
View Scheme
参考文献
Mast, Christian Alexander; Eissler, Stefan; Stoncius, Arvydas; Stammler, Hans-Georg; Neumann, Beate; Sewald, Norbert
Chemistry - A European Journal, 2005 , vol. 11, # 16 p. 4667 - 4677
反应条件
1.1: 99 percent / NaHCO3 / dimethylsulfoxide / 5 h / 60 °C
2.1: 92 percent / DIBALH / toluene / 2 h / -78 °C
3.1: NaH / tetrahydrofuran / 0 - 20 °C
3.2: 85 percent / tetrahydrofuran / 3 h / -78 °C
4.1: 97 percent / p-toluenesulfinic acid / [Pd(PPh3)4] / CH2Cl2 / 2 h / 20 °C
5.1: 93 percent / DMAP; EDC; Et3N / CH2Cl2 / 31 h / 0 - 20 °C
6.1: aq. TFA / CH2Cl2 / 0 - 20 °C
7.1: 77 percent / HATU; DIPEA / dimethylformamide / 1.5 h / 0 - 20 °C
8.1: (CH3O)3CH; PPTS / CH2Cl2 / 2 h / 20 °C
8.2: AcBr / CH2Cl2 / 4 h / 20 °C
8.3: 72 percent / KHCO3; (nBu)4NBr / 1,2-dimethoxy-ethane / 27 h / 40 °C
View Scheme
参考文献
Mast, Christian Alexander; Eissler, Stefan; Stoncius, Arvydas; Stammler, Hans-Georg; Neumann, Beate; Sewald, Norbert
Chemistry - A European Journal, 2005 , vol. 11, # 16 p. 4667 - 4677
反应条件
1.1: 1,4-bis-(9-O-dihydroquinidinyl)phthalazine; K3[Fe(CN)6]; K2OsO4*2H2O / K2CO3; CH3SO2NH2 / 2-methyl-propan-2-ol / 0 °C
1.2: 8.732 g / p-TsOH*H2O / acetone / 20 °C
2.1: 72 percent / Me3SiCl / diethyl ether; hexane / 6 h / -78 °C
3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C
3.2: oxodiperoxymolybdenum(pyridine)-hexamethylphosphorictriamide / tetrahydrofuran / 3 h / -78 °C
4.1: LDA / tetrahydrofuran / 0.33 h / -78 °C
4.2: 85 percent / tetrahydrofuran; dimethylformamide / -78 - 20 °C
5.1: 99 percent / LiAlH4 / tetrahydrofuran / 5 - 20 °C
6.1: 94 percent / DABCO / CH2Cl2 / 20 °C
7.1: 99 percent / NaHCO3 / dimethylsulfoxide / 5 h / 60 °C
8.1: 92 percent / DIBALH / toluene / 2 h / -78 °C
9.1: NaH / tetrahydrofuran / 0 - 20 °C
9.2: 85 percent / tetrahydrofuran / 3 h / -78 °C
10.1: 97 percent / p-toluenesulfinic acid / [Pd(PPh3)4] / CH2Cl2 / 2 h / 20 °C
11.1: 93 percent / DMAP; EDC; Et3N / CH2Cl2 / 31 h / 0 - 20 °C
12.1: aq. TFA / CH2Cl2 / 0 - 20 °C
13.1: 77 percent / HATU; DIPEA / dimethylformamide / 1.5 h / 0 - 20 °C
14.1: (CH3O)3CH; PPTS / CH2Cl2 / 2 h / 20 °C
14.2: AcBr / CH2Cl2 / 4 h / 20 °C
14.3: 72 percent / KHCO3; (nBu)4NBr / 1,2-dimethoxy-ethane / 27 h / 40 °C
View Scheme
参考文献
Mast, Christian Alexander; Eissler, Stefan; Stoncius, Arvydas; Stammler, Hans-Georg; Neumann, Beate; Sewald, Norbert
Chemistry - A European Journal, 2005 , vol. 11, # 16 p. 4667 - 4677
反应条件
1.1: 72 percent / Me3SiCl / diethyl ether; hexane / 6 h / -78 °C
2.1: LDA / tetrahydrofuran / 0.5 h / -78 °C
2.2: oxodiperoxymolybdenum(pyridine)-hexamethylphosphorictriamide / tetrahydrofuran / 3 h / -78 °C
3.1: LDA / tetrahydrofuran / 0.33 h / -78 °C
3.2: 85 percent / tetrahydrofuran; dimethylformamide / -78 - 20 °C
4.1: 99 percent / LiAlH4 / tetrahydrofuran / 5 - 20 °C
5.1: 94 percent / DABCO / CH2Cl2 / 20 °C
6.1: 99 percent / NaHCO3 / dimethylsulfoxide / 5 h / 60 °C
7.1: 92 percent / DIBALH / toluene / 2 h / -78 °C
8.1: NaH / tetrahydrofuran / 0 - 20 °C
8.2: 85 percent / tetrahydrofuran / 3 h / -78 °C
9.1: 97 percent / p-toluenesulfinic acid / [Pd(PPh3)4] / CH2Cl2 / 2 h / 20 °C
10.1: 93 percent / DMAP; EDC; Et3N / CH2Cl2 / 31 h / 0 - 20 °C
11.1: aq. TFA / CH2Cl2 / 0 - 20 °C
12.1: 77 percent / HATU; DIPEA / dimethylformamide / 1.5 h / 0 - 20 °C
13.1: (CH3O)3CH; PPTS / CH2Cl2 / 2 h / 20 °C
13.2: AcBr / CH2Cl2 / 4 h / 20 °C
13.3: 72 percent / KHCO3; (nBu)4NBr / 1,2-dimethoxy-ethane / 27 h / 40 °C
View Scheme
参考文献
Mast, Christian Alexander; Eissler, Stefan; Stoncius, Arvydas; Stammler, Hans-Georg; Neumann, Beate; Sewald, Norbert
Chemistry - A European Journal, 2005 , vol. 11, # 16 p. 4667 - 4677
反应条件
1.1: LDA / tetrahydrofuran / 0.5 h / -78 °C
1.2: oxodiperoxymolybdenum(pyridine)-hexamethylphosphorictriamide / tetrahydrofuran / 3 h / -78 °C
2.1: LDA / tetrahydrofuran / 0.33 h / -78 °C
2.2: 85 percent / tetrahydrofuran; dimethylformamide / -78 - 20 °C
3.1: 99 percent / LiAlH4 / tetrahydrofuran / 5 - 20 °C
4.1: 94 percent / DABCO / CH2Cl2 / 20 °C
5.1: 99 percent / NaHCO3 / dimethylsulfoxide / 5 h / 60 °C
6.1: 92 percent / DIBALH / toluene / 2 h / -78 °C
7.1: NaH / tetrahydrofuran / 0 - 20 °C
7.2: 85 percent / tetrahydrofuran / 3 h / -78 °C
8.1: 97 percent / p-toluenesulfinic acid / [Pd(PPh3)4] / CH2Cl2 / 2 h / 20 °C
9.1: 93 percent / DMAP; EDC; Et3N / CH2Cl2 / 31 h / 0 - 20 °C
10.1: aq. TFA / CH2Cl2 / 0 - 20 °C
11.1: 77 percent / HATU; DIPEA / dimethylformamide / 1.5 h / 0 - 20 °C
12.1: (CH3O)3CH; PPTS / CH2Cl2 / 2 h / 20 °C
12.2: AcBr / CH2Cl2 / 4 h / 20 °C
12.3: 72 percent / KHCO3; (nBu)4NBr / 1,2-dimethoxy-ethane / 27 h / 40 °C
View Scheme
参考文献
Mast, Christian Alexander; Eissler, Stefan; Stoncius, Arvydas; Stammler, Hans-Georg; Neumann, Beate; Sewald, Norbert
Chemistry - A European Journal, 2005 , vol. 11, # 16 p. 4667 - 4677
反应条件
1: sulfuryl chloride
3: 87.5 mg / 1-hydroxybenzotriazole; triethylamine; 1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride / tetrahydrofuran; CH2Cl2 / 0 - 20 °C
4: hydrogen / Pd(OH)2 on carbon / ethyl acetate / 2 h / 20 °C
5: 89 percent / 4-(dimethylamino)pyridine; 1,3-diisopropylcarbodiimide / CH2Cl2 / 18 h / 20 °C
6: CH2Cl2 / 0 - 20 °C
7: 31.0 mg / NaHCO3; diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C
8: 55 percent / dimethyldioxirane / CH2Cl2; acetone / -30 - 20 °C
View Scheme
参考文献
White, James D.; Hong, Jian; Robarge, Lonnie A.
Journal of Organic Chemistry, 1999 , vol. 64, # 17 p. 6206 - 6216
