Cryptophycin 1合成路线 （共 35 条）
反应条件
1.1: aq. TFA / CH2Cl2 / 0 - 20 °C
2.1: 77 percent / HATU; DIPEA / dimethylformamide / 1.5 h / 0 - 20 °C
3.1: (CH3O)3CH; PPTS / CH2Cl2 / 2 h / 20 °C
3.2: AcBr / CH2Cl2 / 4 h / 20 °C
3.3: 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: 59 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 50 h / 40 °C
2: 93 percent / K2CO3 / methanol / 0.5 h
3: 74 percent / 4-dimethylaminopyridine, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) 23 deg C, 16 h
4: CH2Cl2 / 2 h / 23 °C
5: 32 mg / pentafluorophenyl diphenylphosphinate, diisopropylethylamine / dimethylformamide / 16 h / 23 °C
6: 26 mg / m-chloroperoxybenzoic acid / CH2Cl2 / 23 °C
View Scheme
参考文献
Salamonczyk, Grzegorz M.; Han, Kang; Guo, Zhi-Wei; Sih, Charles J.
Journal of Organic Chemistry, 1996 , vol. 61, # 20 p. 6893 - 6900
反应条件
1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C
1.2: tetrahydrofuran; hexane / -78 - 20 °C
2.1: HF-pyridine; pyridine / tetrahydrofuran / 18 h / 20 °C
3.1: Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
4.1: CH2Cl2 / 18 h / 20 °C
5.1: 75 percent / tetra-n-butylammonium fluoride hydrate / tetrahydrofuran / 4.5 h / 20 °C
6.1: 89 percent / 4-(dimethylamino)pyridine; 1,3-diisopropylcarbodiimide / CH2Cl2 / 18 h / 20 °C
7.1: CH2Cl2 / 0 - 20 °C
8.1: 31.0 mg / NaHCO3; diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C
9.1: 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
反应条件
1.1: 97 percent / imidazole / dimethylformamide / 20 °C
2.1: ozone / CH2Cl2 / -78 °C
2.2: dimethyl sulfide / CH2Cl2 / -78 - 20 °C
3.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C
3.2: tetrahydrofuran; hexane / -78 - 20 °C
4.1: HF-pyridine; pyridine / tetrahydrofuran / 18 h / 20 °C
5.1: Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
6.1: CH2Cl2 / 18 h / 20 °C
7.1: 75 percent / tetra-n-butylammonium fluoride hydrate / tetrahydrofuran / 4.5 h / 20 °C
8.1: 89 percent / 4-(dimethylamino)pyridine; 1,3-diisopropylcarbodiimide / CH2Cl2 / 18 h / 20 °C
9.1: CH2Cl2 / 0 - 20 °C
10.1: 31.0 mg / NaHCO3; diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C
11.1: 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
反应条件
1: CH2Cl2 / 18 h / 20 °C
2: 75 percent / tetra-n-butylammonium fluoride hydrate / tetrahydrofuran / 4.5 h / 20 °C
3: 89 percent / 4-(dimethylamino)pyridine; 1,3-diisopropylcarbodiimide / CH2Cl2 / 18 h / 20 °C
4: CH2Cl2 / 0 - 20 °C
5: 31.0 mg / NaHCO3; diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C
6: 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
反应条件
1: 95 percent / imidazole / dimethylformamide / 18 h / 20 °C
2: 77 percent / OsO4; NaIO4 / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 20 h / 20 °C
3: 95 percent / CH2Cl2 / 20 h / 20 °C
4: 92 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 0 - 20 °C
5: 92 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
6: 62 percent / CrCl2 / tetrahydrofuran / 3 h / 0 °C
7: 67 percent / bis(acetonitrile)dichloropalladium(II) / dimethylformamide / 20 h / 20 °C
8: 75 percent / tetra-n-butylammonium fluoride hydrate / tetrahydrofuran / 4.5 h / 20 °C
9: 89 percent / 4-(dimethylamino)pyridine; 1,3-diisopropylcarbodiimide / CH2Cl2 / 18 h / 20 °C
10: CH2Cl2 / 0 - 20 °C
11: 31.0 mg / NaHCO3; diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C
12: 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
反应条件
1.1: ozone / CH2Cl2 / -78 °C
1.2: dimethyl sulfide / CH2Cl2 / -78 - 20 °C
2.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C
2.2: tetrahydrofuran; hexane / -78 - 20 °C
3.1: HF-pyridine; pyridine / tetrahydrofuran / 18 h / 20 °C
4.1: Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
5.1: CH2Cl2 / 18 h / 20 °C
6.1: 75 percent / tetra-n-butylammonium fluoride hydrate / tetrahydrofuran / 4.5 h / 20 °C
7.1: 89 percent / 4-(dimethylamino)pyridine; 1,3-diisopropylcarbodiimide / CH2Cl2 / 18 h / 20 °C
8.1: CH2Cl2 / 0 - 20 °C
9.1: 31.0 mg / NaHCO3; diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C
10.1: 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
反应条件
1: 62 percent / CrCl2 / tetrahydrofuran / 3 h / 0 °C
2: 67 percent / bis(acetonitrile)dichloropalladium(II) / dimethylformamide / 20 h / 20 °C
3: 75 percent / tetra-n-butylammonium fluoride hydrate / tetrahydrofuran / 4.5 h / 20 °C
4: 89 percent / 4-(dimethylamino)pyridine; 1,3-diisopropylcarbodiimide / CH2Cl2 / 18 h / 20 °C
5: CH2Cl2 / 0 - 20 °C
6: 31.0 mg / NaHCO3; diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C
7: 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
反应条件
1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
2: 62 percent / CrCl2 / tetrahydrofuran / 3 h / 0 °C
3: 67 percent / bis(acetonitrile)dichloropalladium(II) / dimethylformamide / 20 h / 20 °C
4: 75 percent / tetra-n-butylammonium fluoride hydrate / tetrahydrofuran / 4.5 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
反应条件
1: 67 percent / bis(acetonitrile)dichloropalladium(II) / dimethylformamide / 20 h / 20 °C
2: 75 percent / tetra-n-butylammonium fluoride hydrate / tetrahydrofuran / 4.5 h / 20 °C
3: 89 percent / 4-(dimethylamino)pyridine; 1,3-diisopropylcarbodiimide / CH2Cl2 / 18 h / 20 °C
4: CH2Cl2 / 0 - 20 °C
5: 31.0 mg / NaHCO3; diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C
6: 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
