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乙二醇
甲醛
63148-62-9
MDI
丁酮
二甲基亚砜
碳酸氢钠
471-34-1
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乙二醇
甲醛
63148-62-9
MDI
丁酮
二甲基亚砜
碳酸氢钠
471-34-1
紫杉醇
合成路线
(共 250 条)
194420-21-8
→
反应条件
33069-62-4
紫杉醇
反应条件
1.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C 2.1: 99 percent / imidazole / dimethylformamide / 0.25 h / 20 °C 3.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C 4.1: 80 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 1 h / 20 °C 5.1: 98 percent / PdCl2; H2O / dimethylformamide / 3.5 h / 20 °C 6.1: 71 percent / TiCl2; LiAlH4 / tetrahydrofuran / 0.33 h / 40 °C 7.1: Na; NH3 / tetrahydrofuran / 2 h / -78 - -45 °C 8.1: TBAF / tetrahydrofuran / 0.08 h / 20 °C 9.1: 100 percent / pyridine / CH2Cl2 / 1.17 h / -45 °C 10.1: 84 percent / DMAP / benzene / 10 h / 35 °C 11.1: HCl; H2O / tetrahydrofuran / 10 h / 60 °C 12.1: pyridine / 0.67 h / 20 °C 13.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C 14.1: DMAP / 4 h / 100 °C 14.2: DMAP / toluene / 4 h / 100 °C 15.1: P(OMe)3 / 5 h / 110 °C 16.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C 17.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C 18.1: 98 percent / pyridine / 0.17 h / -23 °C 19.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C 20.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C 21.1: 42 percent / DBU / toluene / 1.75 h / 50 °C 22.1: 91 percent / DMAP; pyridine / 13 h / 20 °C 23.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C 24.1: 96 percent / HF*pyridine / tetrahydrofuran / 1 h / 20 °C 25.1: 87 percent / pyridine / 0.5 h / 20 °C 26.1: 66 percent / DPTC; DMAP / toluene / 4 h / 73 °C 27.1: 76 percent / H2 / Pd(OH)2/C / ethanol / 23 h / 20 °C 28.1: 100 percent / HCl; H2O / ethanol / 2 h / 20 °C View Scheme
参考文献
Chemistry - A European Journal, , vol. 5, # 1 p. 121 - 161
194420-16-1
→
反应条件
33069-62-4
紫杉醇
反应条件
1.1: 90 percent / MeONa / methanol / 1 h / 0 °C 2.1: 94 percent / AlH3 / toluene; tetrahydrofuran / 2 h / -78 °C 3.1: 100 percent / CSA / CH2Cl2 / 1 h / 20 °C 4.1: 97 percent / DDQ; H2O / CH2Cl2 / 1 h / 20 °C 5.1: 90 percent / PDC / CH2Cl2 / 16 h / 20 °C 6.1: s-BuLi / cyclohexane / 0.42 h / -23 °C 6.2: 96 percent / cyclohexane; benzene / 1 h / 0 °C 7.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C 8.1: 99 percent / imidazole / dimethylformamide / 0.25 h / 20 °C 9.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C 10.1: 80 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 1 h / 20 °C 11.1: 98 percent / PdCl2; H2O / dimethylformamide / 3.5 h / 20 °C 12.1: 71 percent / TiCl2; LiAlH4 / tetrahydrofuran / 0.33 h / 40 °C 13.1: Na; NH3 / tetrahydrofuran / 2 h / -78 - -45 °C 14.1: TBAF / tetrahydrofuran / 0.08 h / 20 °C 15.1: 100 percent / pyridine / CH2Cl2 / 1.17 h / -45 °C 16.1: 84 percent / DMAP / benzene / 10 h / 35 °C 17.1: HCl; H2O / tetrahydrofuran / 10 h / 60 °C 18.1: pyridine / 0.67 h / 20 °C 19.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C 20.1: DMAP / 4 h / 100 °C 20.2: DMAP / toluene / 4 h / 100 °C 21.1: P(OMe)3 / 5 h / 110 °C 22.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C 23.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C 24.1: 98 percent / pyridine / 0.17 h / -23 °C 25.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C 26.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C 27.1: 42 percent / DBU / toluene / 1.75 h / 50 °C 28.1: 91 percent / DMAP; pyridine / 13 h / 20 °C 29.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C 30.1: 96 percent / HF*pyridine / tetrahydrofuran / 1 h / 20 °C 31.1: 87 percent / pyridine / 0.5 h / 20 °C 32.1: 66 percent / DPTC; DMAP / toluene / 4 h / 73 °C 33.1: 76 percent / H2 / Pd(OH)2/C / ethanol / 23 h / 20 °C 34.1: 100 percent / HCl; H2O / ethanol / 2 h / 20 °C View Scheme
参考文献
Chemistry - A European Journal, , vol. 5, # 1 p. 121 - 161
222726-93-4
→
反应条件
33069-62-4
紫杉醇
反应条件
1.1: 92 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h / 0 °C 2.1: 90 percent / MeONa / methanol / 1 h / 0 °C 3.1: 94 percent / AlH3 / toluene; tetrahydrofuran / 2 h / -78 °C 4.1: 100 percent / CSA / CH2Cl2 / 1 h / 20 °C 5.1: 97 percent / DDQ; H2O / CH2Cl2 / 1 h / 20 °C 6.1: 90 percent / PDC / CH2Cl2 / 16 h / 20 °C 7.1: s-BuLi / cyclohexane / 0.42 h / -23 °C 7.2: 96 percent / cyclohexane; benzene / 1 h / 0 °C 8.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C 9.1: 99 percent / imidazole / dimethylformamide / 0.25 h / 20 °C 10.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C 11.1: 80 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 1 h / 20 °C 12.1: 98 percent / PdCl2; H2O / dimethylformamide / 3.5 h / 20 °C 13.1: 71 percent / TiCl2; LiAlH4 / tetrahydrofuran / 0.33 h / 40 °C 14.1: Na; NH3 / tetrahydrofuran / 2 h / -78 - -45 °C 15.1: TBAF / tetrahydrofuran / 0.08 h / 20 °C 16.1: 100 percent / pyridine / CH2Cl2 / 1.17 h / -45 °C 17.1: 84 percent / DMAP / benzene / 10 h / 35 °C 18.1: HCl; H2O / tetrahydrofuran / 10 h / 60 °C 19.1: pyridine / 0.67 h / 20 °C 20.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C 21.1: DMAP / 4 h / 100 °C 21.2: DMAP / toluene / 4 h / 100 °C 22.1: P(OMe)3 / 5 h / 110 °C 23.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C 24.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C 25.1: 98 percent / pyridine / 0.17 h / -23 °C 26.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C 27.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C 28.1: 42 percent / DBU / toluene / 1.75 h / 50 °C 29.1: 91 percent / DMAP; pyridine / 13 h / 20 °C 30.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C 31.1: 96 percent / HF*pyridine / tetrahydrofuran / 1 h / 20 °C 32.1: 87 percent / pyridine / 0.5 h / 20 °C 33.1: 66 percent / DPTC; DMAP / toluene / 4 h / 73 °C 34.1: 76 percent / H2 / Pd(OH)2/C / ethanol / 23 h / 20 °C 35.1: 100 percent / HCl; H2O / ethanol / 2 h / 20 °C View Scheme
参考文献
Chemistry - A European Journal, , vol. 5, # 1 p. 121 - 161
194420-15-0
→
反应条件
33069-62-4
紫杉醇
反应条件
1.1: 97 percent / HCl; H2O / tetrahydrofuran / 0.83 h / 0 °C 2.1: 92 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h / 0 °C 3.1: 90 percent / MeONa / methanol / 1 h / 0 °C 4.1: 94 percent / AlH3 / toluene; tetrahydrofuran / 2 h / -78 °C 5.1: 100 percent / CSA / CH2Cl2 / 1 h / 20 °C 6.1: 97 percent / DDQ; H2O / CH2Cl2 / 1 h / 20 °C 7.1: 90 percent / PDC / CH2Cl2 / 16 h / 20 °C 8.1: s-BuLi / cyclohexane / 0.42 h / -23 °C 8.2: 96 percent / cyclohexane; benzene / 1 h / 0 °C 9.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C 10.1: 99 percent / imidazole / dimethylformamide / 0.25 h / 20 °C 11.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C 12.1: 80 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 1 h / 20 °C 13.1: 98 percent / PdCl2; H2O / dimethylformamide / 3.5 h / 20 °C 14.1: 71 percent / TiCl2; LiAlH4 / tetrahydrofuran / 0.33 h / 40 °C 15.1: Na; NH3 / tetrahydrofuran / 2 h / -78 - -45 °C 16.1: TBAF / tetrahydrofuran / 0.08 h / 20 °C 17.1: 100 percent / pyridine / CH2Cl2 / 1.17 h / -45 °C 18.1: 84 percent / DMAP / benzene / 10 h / 35 °C 19.1: HCl; H2O / tetrahydrofuran / 10 h / 60 °C 20.1: pyridine / 0.67 h / 20 °C 21.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C 22.1: DMAP / 4 h / 100 °C 22.2: DMAP / toluene / 4 h / 100 °C 23.1: P(OMe)3 / 5 h / 110 °C 24.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C 25.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C 26.1: 98 percent / pyridine / 0.17 h / -23 °C 27.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C 28.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C 29.1: 42 percent / DBU / toluene / 1.75 h / 50 °C 30.1: 91 percent / DMAP; pyridine / 13 h / 20 °C 31.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C 32.1: 96 percent / HF*pyridine / tetrahydrofuran / 1 h / 20 °C 33.1: 87 percent / pyridine / 0.5 h / 20 °C 34.1: 66 percent / DPTC; DMAP / toluene / 4 h / 73 °C 35.1: 76 percent / H2 / Pd(OH)2/C / ethanol / 23 h / 20 °C 36.1: 100 percent / HCl; H2O / ethanol / 2 h / 20 °C View Scheme
参考文献
Chemistry - A European Journal, , vol. 5, # 1 p. 121 - 161
202390-88-3
→
反应条件
33069-62-4
紫杉醇
反应条件
water; trifluoroacetic acid T=0°C;
参考文献
Shiina, Isamu; Saitoh, Katsuyuki; Frechard-Ortuno, Isabelle; Mukaiyama, Teruaki
Chemistry Letters, 1998 , # 1 p. 3 - 4
155588-19-5
→
反应条件
33069-62-4
紫杉醇
反应条件
1: 85 percent / pyridine / toluene / 0.5 h / 0 °C 2: 95 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 0.5 h / 25 °C 3: tetrahydrofuran; cyclohexane / 15 h / -78 °C 4: 94 percent Turnov. / NaBH4 / methanol / 3 h / 25 °C 5: 86 percent Turnov. / NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / 0 °C 6: 80 percent / HF*pyridine / tetrahydrofuran / 1.25 h / 25 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 117, # 2 p. 624 - 633
155588-21-9
→
反应条件
33069-62-4
紫杉醇
反应条件
1: 93 percent Turnov. / aq. K2CO3 / methanol / 2.5 h / 0 °C 2: 85 percent / pyridine / toluene / 0.5 h / 0 °C 3: 95 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 0.5 h / 25 °C 4: tetrahydrofuran; cyclohexane / 15 h / -78 °C 5: 94 percent Turnov. / NaBH4 / methanol / 3 h / 25 °C 6: 86 percent Turnov. / NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / 0 °C 7: 80 percent / HF*pyridine / tetrahydrofuran / 1.25 h / 25 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 117, # 2 p. 624 - 633
219780-94-6
→
反应条件
33069-62-4
紫杉醇
反应条件
1: 94 percent / pyridine / CH2Cl2 / 1 h / -78 - 0 °C 2: 66 percent / DMAP / CH2Cl2 / 6 h / 20 °C 3: 83 percent / tetrahydrofuran / 0.33 h / -78 °C 4: 88 percent / HF*pyridine / tetrahydrofuran / 2 h / 20 °C 5: 94 percent / pyridine / CH2Cl2 / 3 h / 20 °C 6: 80 percent / TASF / tetrahydrofuran / 48 h / 20 °C 7: 77 percent / LHMDS / tetrahydrofuran / -78 - 0 °C 8: 84 percent / Zn; aq. AcOH / 16 h / 20 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 122, # 16 p. 3811 - 3820
219780-97-9
→
反应条件
33069-62-4
紫杉醇
反应条件
1: 94 percent / pyridine / CH2Cl2 / 3 h / 20 °C 2: 80 percent / TASF / tetrahydrofuran / 48 h / 20 °C 3: 77 percent / LHMDS / tetrahydrofuran / -78 - 0 °C 4: 84 percent / Zn; aq. AcOH / 16 h / 20 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 122, # 16 p. 3811 - 3820
219780-95-7
→
反应条件
33069-62-4
紫杉醇
反应条件
1: 66 percent / DMAP / CH2Cl2 / 6 h / 20 °C 2: 83 percent / tetrahydrofuran / 0.33 h / -78 °C 3: 88 percent / HF*pyridine / tetrahydrofuran / 2 h / 20 °C 4: 94 percent / pyridine / CH2Cl2 / 3 h / 20 °C 5: 80 percent / TASF / tetrahydrofuran / 48 h / 20 °C 6: 77 percent / LHMDS / tetrahydrofuran / -78 - 0 °C 7: 84 percent / Zn; aq. AcOH / 16 h / 20 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 122, # 16 p. 3811 - 3820
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