Epothilone D 合成路线 （共 263 条）
189453-35-8 (4S,7R,8S,9S,13Z,16S)-4,8-二-{[叔-丁基(二甲基)硅烷基]氧基}-5,5,7,9,13-五甲基-16-[(E)-1-甲基-2-(2-甲基-1,3-噻唑-4-基)乙烯基]氧代环己癸-13-烯-2,6-二酮
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反应条件
反应条件
pyridine hydrogenfluoride in tetrahydrofuran T=20°C; 36 h;
参考文献
Mulzer, Johann; Mantoulidis, Andreas; Oehler, Elisabeth
反应条件
TrisNHNH2; triethylamine in 1,2-dichloro-ethane T=50°C; 7 h;
参考文献
SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH
反应条件
1: EDC; DMAP / CH2Cl2 2: 59 percent / second-generation Grubbs catalyst / CH2Cl2 / 6 h / Heating 3: TFA / CH2Cl2 / 0 - 20 °C View Scheme
参考文献
Tetrahedron Letters, , vol. 45, # 9 p. 1945 - 1947
反应条件
1.1: 88 percent / Bu2BOTf; DIPEA / CH2Cl2 / 1 h / -78 °C 2.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 3.1: 76 percent / lithium hydroxide; hydrogen peroxide / tetrahydrofuran; H2O / 4 h / 20 °C 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 4.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 5.1: pyridine / CH2Cl2 / 1 h / 0 °C 6.1: CH2Cl2 / 5 h / 20 °C 7.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 8.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 9.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 10.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 11.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 69, # 26 p. 9269 - 9284
反应条件
1.1: tributylphosphine oxide / diethylaluminum chloride; R(a)-[2,2'-dihydroxy-3,3'-bis(CH2Ph2PO)]-1,1'-binaphthyl / CH2Cl2; hexane / 0.5 h / -40 °C 1.2: CH2Cl2; hexane / 39 h 1.3: 97 percent / trifluoroacetic acid / CH2Cl2; hexane / 1 h / 20 °C 2.1: 83 percent / aq. HCl / 5 h / 90 °C 3.1: 99 percent / imidazole / dimethylformamide / 3 h / 20 °C 4.1: 94 percent / DIBAL / toluene / 1 h / -78 °C 5.1: 68 percent / tetrahydrofuran / -78 - 20 °C 6.1: Hg(OAc)2; water / tetrahydrofuran / 2.5 h 6.2: 60 percent / tetrabutylammonium iodide / tetrahydrofuran; H2O / 2 h 7.1: 100 percent / HF-pyridine / tetrahydrofuran / 12 h / 20 °C 8.1: 96 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C 9.1: 9-BBN / tetrahydrofuran / 1.5 h / 28 °C / microwave irradiation 9.2: 37 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 1 h / 60 °C 10.1: 93 percent / aq. NaOH / methanol / 36 h / 50 °C 11.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 11.2: 90 percent / DMAP / toluene; tetrahydrofuran / 1 h 12.1: 92 percent / HF*pyridine / tetrahydrofuran View Scheme
参考文献
Journal of the American Chemical Society, , vol. 122, # 43 p. 10521 - 10532
反应条件
1.1: Et3N / CH2Cl2 / 0.17 h / 0 °C 2.1: 84 percent / LiBr / acetone; CH2Cl2 / 1.8 h / 20 °C 3.1: CuI; Et3N / diethyl ether; dimethylformamide / 20 °C 3.2: 60 percent / diethyl ether; dimethylformamide / 18 h / 20 °C 4.1: 68 percent / H2; Pb(OAc)2 / Pd/CaCO3 / hexane / 28 h / 20 °C 5.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C 6.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 7.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 7.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 8.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 9.1: 52 percent / KO2CN=NCO2K; AcOH / CH2Cl2 / 25 h / Heating View Scheme
参考文献
Journal of the American Chemical Society, , vol. 123, # 23 p. 5407 - 5413
反应条件
pyridine hydrogenfluoride in tetrahydrofuran T=20°C; 16 h;
参考文献
Jung, Jae-Chul; Kache, Rajashaker; Vines, Kimberly K.; Zheng, Yan-Song; Bijoy, Panicker; Valluri, Muralikrishna; Avery, Mitchell A.
反应条件
potassium diazodicarboxylate; acetic acid in dichloromethane Heating;
参考文献
Biswas, Kaustav; Lin, Hong; Njardarson, Jon T.; Chappell, Mark D.; Chou, Ting-Chao; Guan, Yongbiao; Tong, William P.; He, Lifeng; Horwitz, Susan B.; Danishefsky, Samuel J.
反应条件
1.1: tetrahydrofuran / -78 °C 2.1: LiHMDS / tetrahydrofuran / -78 °C 2.2: 80 percent / tetrahydrofuran 3.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 3.2: 85 percent / nBu4NF / tetrahydrofuran 4.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 4.2: 60 percent / DMAP / toluene / 80 °C 5.1: 86 percent / TFA / CH2Cl2 / 0 °C 6.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme
参考文献
Tetrahedron Letters, , vol. 43, # 16 p. 2895 - 2898
反应条件
1.1: i-Pr2NH; n-BuLi / tetrahydrofuran; hexane / 0.83 h / -78 °C 1.2: 61 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.1: 89 percent / Et3N / CH2Cl2 / 0.75 h / 0 °C 3.1: OsO4; NaIO4 / tetrahydrofuran; H2O / 18 h 4.1: NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 1 h 5.1: 502 mg / methanol; benzene; hexane / 0.75 h 6.1: 92 percent / H2 / Pd/C / ethanol / 0.75 h 7.1: 99 percent / TPAP; NMO / CH2Cl2 / 1 h 8.1: hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / -78 - -30 °C 8.2: 82 percent / tetrahydrofuran; hexane / 70 h / -78 - 20 °C 9.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C 10.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 11.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 11.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 12.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 13.1: 52 percent / KO2CN=NCO2K; AcOH / CH2Cl2 / 25 h / Heating View Scheme
参考文献
Journal of the American Chemical Society, , vol. 123, # 23 p. 5407 - 5413
