(5S)-3-[(2S,13R)-2,13-二羟基-13-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-羟基十一烷基]四氢呋喃-2-基]四氢呋喃-2-基]十三烷基]-5-甲基-5H-呋喃-2-酮合成路线 （共 102 条）
反应条件
hydrogen fluoride in tetrahydrofuran; acetonitrile T=20°C; 12 h; Inert atmosphere;
参考文献
Sinha, Subhash C.; Chen, Zhiyong; Huang, Zheng-Zheng; Nakamaru-Ogiso, Eiko; Pietraszkiewicz, Halina; Edelstein, Matthew; Valeriote, Frederick
Journal of Medicinal Chemistry, 2008 , vol. 51, # 22 p. 7045 - 7048
反应条件
pyridinium p-toluenesulfonate in ethanol T=40°C; 16 h;
参考文献
Marshall, James A.; Hinkle, Kevin W.
Journal of Organic Chemistry, 1997 , vol. 62, # 17 p. 5989 - 5995
反应条件
hydrogenchloride in tetrahydrofuran; methanol T=20°C; 15 h;
参考文献
Marshall, James A.; Piettre, Arnaud; Paige, Mikell A.; Valeriote, Frederick
Journal of Organic Chemistry, 2003 , vol. 68, # 5 p. 1771 - 1779
反应条件
1: 4 Angstroem molecular sieves; SnCl4 / CH2Cl2 / -40 °C 2: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C 3: 0.5 h / 20 °C 4: Pd(PPh3)4; water / tetrahydrofuran / 2 h / 20 °C 5: AgNO3/SiO2 / hexane; CH2Cl2 / 2 h 6: KCN / methanol / 0.33 h View Scheme
参考文献
Journal of the American Chemical Society, , vol. 127, # 31 p. 10818 - 10819
反应条件
1: diisopropylethyl amine; DMSO; SO3*pyridine / CH2Cl2 / 1 h / 0 °C 2: 4 Angstroem molecular sieves; SnCl4 / CH2Cl2 / -40 °C 3: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C 4: 0.5 h / 20 °C 5: Pd(PPh3)4; water / tetrahydrofuran / 2 h / 20 °C 6: AgNO3/SiO2 / hexane; CH2Cl2 / 2 h 7: KCN / methanol / 0.33 h View Scheme
参考文献
Journal of the American Chemical Society, , vol. 127, # 31 p. 10818 - 10819
反应条件
1: Pd(OH)2; H2 / tetrahydrofuran / 2 h / 20 °C 2: diisopropylethyl amine; DMSO; SO3*pyridine / CH2Cl2 / 1 h / 0 °C 3: 4 Angstroem molecular sieves; SnCl4 / CH2Cl2 / -40 °C 4: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C 5: 0.5 h / 20 °C 6: Pd(PPh3)4; water / tetrahydrofuran / 2 h / 20 °C 7: AgNO3/SiO2 / hexane; CH2Cl2 / 2 h 8: KCN / methanol / 0.33 h View Scheme
参考文献
Journal of the American Chemical Society, , vol. 127, # 31 p. 10818 - 10819
反应条件
1: 4 Angstroem molecular sieves; SnCl4 / CH2Cl2 / -40 °C 2: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C 3: 0.5 h / 20 °C 4: Pd(PPh3)4; water / tetrahydrofuran / 2 h / 20 °C 5: AgNO3/SiO2 / hexane; CH2Cl2 / 2 h 6: KCN / methanol / 0.33 h View Scheme
参考文献
Journal of the American Chemical Society, , vol. 127, # 31 p. 10818 - 10819
反应条件
1.1: BF3*Et2O / tetrahydrofuran; hexane / 0.08 h / -78 °C 1.2: tetrahydrofuran; hexane / 4 h / -78 °C 1.3: 340 mg / aq. H2O2 / tetrahydrofuran; hexane; aq. phosphate buffer / 16 h / 20 °C 2.1: 85 percent / imidazole / various solvent(s) / 72 h / 40 °C 3.1: 4 Angstroem molecular sieves; SnCl4 / CH2Cl2 / -40 °C 4.1: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C 5.1: 0.5 h / 20 °C 6.1: Pd(PPh3)4; water / tetrahydrofuran / 2 h / 20 °C 7.1: AgNO3/SiO2 / hexane; CH2Cl2 / 2 h 8.1: KCN / methanol / 0.33 h View Scheme
参考文献
Journal of the American Chemical Society, , vol. 127, # 31 p. 10818 - 10819
反应条件
1.1: 93 percent / triethylamine; DMAP / CH2Cl2 / 24 h / 20 °C 2.1: 97 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 0.5 h / -78 °C 3.1: 97 percent / DMSO; diisopropylethylamine; SO3*pyridine / CH2Cl2 / 1 h / 0 °C 4.1: BF3*Et2O / tetrahydrofuran; hexane / 0.08 h / -78 °C 4.2: tetrahydrofuran; hexane / 4 h / -78 °C 4.3: 340 mg / aq. H2O2 / tetrahydrofuran; hexane; aq. phosphate buffer / 16 h / 20 °C 5.1: 85 percent / imidazole / various solvent(s) / 72 h / 40 °C 6.1: 4 Angstroem molecular sieves; SnCl4 / CH2Cl2 / -40 °C 7.1: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C 8.1: 0.5 h / 20 °C 9.1: Pd(PPh3)4; water / tetrahydrofuran / 2 h / 20 °C 10.1: AgNO3/SiO2 / hexane; CH2Cl2 / 2 h 11.1: KCN / methanol / 0.33 h View Scheme
参考文献
Journal of the American Chemical Society, , vol. 127, # 31 p. 10818 - 10819
反应条件
1.1: 97 percent / DMSO; diisopropylethylamine; SO3*pyridine / CH2Cl2 / 1 h / 0 °C 2.1: BF3*Et2O / tetrahydrofuran; hexane / 0.08 h / -78 °C 2.2: tetrahydrofuran; hexane / 4 h / -78 °C 2.3: 340 mg / aq. H2O2 / tetrahydrofuran; hexane; aq. phosphate buffer / 16 h / 20 °C 3.1: 85 percent / imidazole / various solvent(s) / 72 h / 40 °C 4.1: 4 Angstroem molecular sieves; SnCl4 / CH2Cl2 / -40 °C 5.1: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C 6.1: 0.5 h / 20 °C 7.1: Pd(PPh3)4; water / tetrahydrofuran / 2 h / 20 °C 8.1: AgNO3/SiO2 / hexane; CH2Cl2 / 2 h 9.1: KCN / methanol / 0.33 h View Scheme
参考文献
Journal of the American Chemical Society, , vol. 127, # 31 p. 10818 - 10819
