(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
1: m-CPBA / CH2Cl2 / 0.5 h / 0 °C 2: 0.191 g / toluene / 1 h / Heating 3: 89 percent / HF*pyridine / tetrahydrofuran / 25 h / 20 °C 4: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 5: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 6: 57 percent / aq. HCl / methanol; tetrahydrofuran / 15 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 5 p. 1771 - 1779
反应条件
1: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 2: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 3: 57 percent / aq. HCl / methanol; tetrahydrofuran / 15 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 5 p. 1771 - 1779
反应条件
1: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 2: 57 percent / aq. HCl / methanol; tetrahydrofuran / 15 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 5 p. 1771 - 1779
反应条件
1: 89 percent / pyridine / 21 h / 20 °C 2: 70 percent / TBAF / tetrahydrofuran / 18 h / 40 °C 3: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 4: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 5: 57 percent / aq. HCl / methanol; tetrahydrofuran / 15 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 5 p. 1771 - 1779
反应条件
1: 70 percent / TBAF / tetrahydrofuran / 18 h / 40 °C 2: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 3: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 4: 57 percent / aq. HCl / methanol; tetrahydrofuran / 15 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 5 p. 1771 - 1779
反应条件
1: 97 percent / I2, Ph3P, imidazole / CH2Cl2; benzene / 1 h 2: 91 percent / tetrahydrofuran / 12 h / 0 °C 3: 100 percent / (DHQD)2AQN, K2Fe3(CN)6, K2CO3, K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 12 h / 0 °C 4: 19 percent / pyridine / 10 h / Ambient temperature 5: 79 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 6: 1.) BF3*OEt2 / 1.) THF, -78 deg C, 10 min, 2.) THF, 20 min 7: i-Pr2NEt / CH2Cl2 / 12 h / Ambient temperature 8: TBAF / tetrahydrofuran / 6 h / 40 °C 9: 2,6-lutidine / tetrahydrofuran / 0.33 h 10: 1.) Pd(PPh3)4, H2O, 2.) AgNO3/SiO2 / 1.) THF, 1.7 h, 2.) CH2Cl2, hexane, 2 h 11: 67 percent / PPTS / ethanol / 16 h / 40 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 62, # 17 p. 5989 - 5995
反应条件
1: 91 percent / tetrahydrofuran / 12 h / 0 °C 2: 100 percent / (DHQD)2AQN, K2Fe3(CN)6, K2CO3, K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 12 h / 0 °C 3: 19 percent / pyridine / 10 h / Ambient temperature 4: 79 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 5: 1.) BF3*OEt2 / 1.) THF, -78 deg C, 10 min, 2.) THF, 20 min 6: i-Pr2NEt / CH2Cl2 / 12 h / Ambient temperature 7: TBAF / tetrahydrofuran / 6 h / 40 °C 8: 2,6-lutidine / tetrahydrofuran / 0.33 h 9: 1.) Pd(PPh3)4, H2O, 2.) AgNO3/SiO2 / 1.) THF, 1.7 h, 2.) CH2Cl2, hexane, 2 h 10: 67 percent / PPTS / ethanol / 16 h / 40 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 62, # 17 p. 5989 - 5995
反应条件
1: 1.) BF3*OEt2 / 1.) THF, -78 deg C, 10 min, 2.) THF, 20 min 2: i-Pr2NEt / CH2Cl2 / 12 h / Ambient temperature 3: TBAF / tetrahydrofuran / 6 h / 40 °C 4: 2,6-lutidine / tetrahydrofuran / 0.33 h 5: 1.) Pd(PPh3)4, H2O, 2.) AgNO3/SiO2 / 1.) THF, 1.7 h, 2.) CH2Cl2, hexane, 2 h 6: 67 percent / PPTS / ethanol / 16 h / 40 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 62, # 17 p. 5989 - 5995
反应条件
1: 100 percent / (DHQD)2AQN, K2Fe3(CN)6, K2CO3, K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 12 h / 0 °C 2: 19 percent / pyridine / 10 h / Ambient temperature 3: 79 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 4: 1.) BF3*OEt2 / 1.) THF, -78 deg C, 10 min, 2.) THF, 20 min 5: i-Pr2NEt / CH2Cl2 / 12 h / Ambient temperature 6: TBAF / tetrahydrofuran / 6 h / 40 °C 7: 2,6-lutidine / tetrahydrofuran / 0.33 h 8: 1.) Pd(PPh3)4, H2O, 2.) AgNO3/SiO2 / 1.) THF, 1.7 h, 2.) CH2Cl2, hexane, 2 h 9: 67 percent / PPTS / ethanol / 16 h / 40 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 62, # 17 p. 5989 - 5995
反应条件
1: 19 percent / pyridine / 10 h / Ambient temperature 2: 79 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 3: 1.) BF3*OEt2 / 1.) THF, -78 deg C, 10 min, 2.) THF, 20 min 4: i-Pr2NEt / CH2Cl2 / 12 h / Ambient temperature 5: TBAF / tetrahydrofuran / 6 h / 40 °C 6: 2,6-lutidine / tetrahydrofuran / 0.33 h 7: 1.) Pd(PPh3)4, H2O, 2.) AgNO3/SiO2 / 1.) THF, 1.7 h, 2.) CH2Cl2, hexane, 2 h 8: 67 percent / PPTS / ethanol / 16 h / 40 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 62, # 17 p. 5989 - 5995
