1α,25-二羟基-2β-(3-羟基丙氧基)维生素D3合成路线 (共 32 条)
反应条件
1.1: 88 percent / Me4NOH; aq. NaOH / toluene / 72 h / 20 °C 2.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C 3.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h 4.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C 5.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C 6.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h 7.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C 8.1: Mg / tetrahydrofuran / 0.5 h / 20 °C 8.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C 9.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 123, # 16 p. 3716 - 3722
反应条件
1.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C 2.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C 3.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h 4.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C 5.1: Mg / tetrahydrofuran / 0.5 h / 20 °C 5.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C 6.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 123, # 16 p. 3716 - 3722
反应条件
1.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C 2.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h 3.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C 4.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C 5.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h 6.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C 7.1: Mg / tetrahydrofuran / 0.5 h / 20 °C 7.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C 8.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 123, # 16 p. 3716 - 3722
反应条件
1.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C 2.1: Mg / tetrahydrofuran / 0.5 h / 20 °C 2.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C 3.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 123, # 16 p. 3716 - 3722
反应条件
1.1: 2.1 g / Et3N; DMAP / CH2Cl2 / 3 h / 20 °C 2.1: 91 percent / BaCO3; NBS / CCl4 / Heating 3.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C 4.1: pyridine / 20 °C 5.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C 6.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 6.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C 6.3: 90 percent / K2CO3 / methanol / 20 °C 7.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C 8.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating 9.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 69, # 22 p. 7463 - 7471
反应条件
1.1: 91 percent / BaCO3; NBS / CCl4 / Heating 2.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C 3.1: pyridine / 20 °C 4.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C 5.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 5.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C 5.3: 90 percent / K2CO3 / methanol / 20 °C 6.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C 7.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating 8.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 69, # 22 p. 7463 - 7471
反应条件
1.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C 2.1: pyridine / 20 °C 3.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C 4.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 4.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C 4.3: 90 percent / K2CO3 / methanol / 20 °C 5.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C 6.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating 7.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 69, # 22 p. 7463 - 7471
反应条件
1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating 2: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 69, # 22 p. 7463 - 7471
反应条件
1.1: KOt-Bu / 110 °C 2.1: 2.1 g / Et3N; DMAP / CH2Cl2 / 3 h / 20 °C 3.1: 91 percent / BaCO3; NBS / CCl4 / Heating 4.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C 5.1: pyridine / 20 °C 6.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C 7.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 7.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C 7.3: 90 percent / K2CO3 / methanol / 20 °C 8.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C 9.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating 10.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 69, # 22 p. 7463 - 7471
反应条件
1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C 2: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating 3: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 69, # 22 p. 7463 - 7471