(3S,4S)-3-己基-4-[(S)-2-羟基十三烷基]-2-氧杂环丁酮合成路线 （共 120 条）
反应条件
1: 73 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / -10 - 20 °C 2: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature 3: benzenesulfonylchloride, pyridine / 0 °C 4: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 53, # 6 p. 1218 - 1221
反应条件
1: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature 2: benzenesulfonylchloride, pyridine / 0 °C 3: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 53, # 6 p. 1218 - 1221
反应条件
1: Jones' reagent / acetone / 1 h / 10 °C 2: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature 3: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C 4: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h 5: 73 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / -10 - 20 °C 6: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature 7: benzenesulfonylchloride, pyridine / 0 °C 8: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 53, # 6 p. 1218 - 1221
反应条件
1: 1) 2.4 eq. n-BuLi; 2) 1.4 M H2SO4 / 1) THF, -78 deg C; 2) from -20 deg C to room temperature 2: 1) 2 eq. dicyclohexylborane; 2) NaOH, H2O2 / 1) THF, 0 deg C; 2) 40-50 deg C 3: HCl / 2 h / Ambient temperature 4: 0.1 eq. triflic acid / CH2Cl2; cyclohexane / 10 - 20 °C 5: 1.1 eq. DiBALH / CH2Cl2 / -78 °C 6: 83 percent / BF3*Et2O / diethyl ether / 3 h / -15 - 5 °C 7: 61 percent / 1.1 eq. TBAF / tetrahydrofuran / 0.02 h / 80 °C 8: 88 percent / H2 / Pd-C / tetrahydrofuran / 8 h / Ambient temperature View Scheme
参考文献
Tetrahedron Letters, , vol. 30, # 14 p. 1833 - 1836
反应条件
1: With zinc(II) chloride in dichloromethane T=23°C; Mukaiyama aldol-lactonization; 60 h; Inert atmosphere; 2: With hydrogen fluoride in acetonitrile T=0 - 23°C; Inert atmosphere; optical yield given as percent de;
参考文献
Richardson, Robyn D.; Knowles, Lynn M.; Cieplak, Piotr; Smith, Jeffrey W.; Ma, Gil; Oyola, Yatsandra; Zancanella, Manuel; Romo, Daniel
Journal of Medicinal Chemistry, 2008 , vol. 51, # 17 p. 5285 - 5296
反应条件
1.1: NaH / 4 h 1.2: 78 percent / 12 h 2.1: 79 percent / AIBN; n-Bu3SnH / toluene / 1.5 h / Heating 3.1: 98 percent / TBAF / tetrahydrofuran / 2 h / 25 °C 4.1: 92 percent / Et3N / CH2Cl2 / 3 h / 20 °C 5.1: 76 percent / CuBr / tetrahydrofuran; diethyl ether / 5 h / 20 °C 6.1: 72 percent / aq. AcOH / 4 h / Heating 7.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 8.1: Et3N / 10 h / 20 °C 9.1: 71 percent / DIPEA; DMAP / CH2Cl2 / 6 h / 20 °C 10.1: 94 percent / H2 / Pd(OH)2/C / ethyl acetate / 12 h 11.1: LDA / tetrahydrofuran / 1 h / -50 °C 11.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -50 - 0 °C 12.1: LiOH; H2O / tetrahydrofuran; methanol / 12 h / 0 - 20 °C 13.1: 210 mg / PhSO2Cl; pyridine / 12 h / 0 °C 14.1: 88 percent / BF3*Et2O; ethane-1,2-dithiol / CH2Cl2 / 1 h / 0 °C View Scheme
参考文献
Synthesis, , # 22 p. 3888 - 3894
反应条件
1.1: 79 percent / AIBN; n-Bu3SnH / toluene / 1.5 h / Heating 2.1: 98 percent / TBAF / tetrahydrofuran / 2 h / 25 °C 3.1: 92 percent / Et3N / CH2Cl2 / 3 h / 20 °C 4.1: 76 percent / CuBr / tetrahydrofuran; diethyl ether / 5 h / 20 °C 5.1: 72 percent / aq. AcOH / 4 h / Heating 6.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 7.1: Et3N / 10 h / 20 °C 8.1: 71 percent / DIPEA; DMAP / CH2Cl2 / 6 h / 20 °C 9.1: 94 percent / H2 / Pd(OH)2/C / ethyl acetate / 12 h 10.1: LDA / tetrahydrofuran / 1 h / -50 °C 10.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -50 - 0 °C 11.1: LiOH; H2O / tetrahydrofuran; methanol / 12 h / 0 - 20 °C 12.1: 210 mg / PhSO2Cl; pyridine / 12 h / 0 °C 13.1: 88 percent / BF3*Et2O; ethane-1,2-dithiol / CH2Cl2 / 1 h / 0 °C View Scheme
参考文献
Synthesis, , # 22 p. 3888 - 3894
反应条件
1.1: 76 percent / CuBr / tetrahydrofuran; diethyl ether / 5 h / 20 °C 2.1: 72 percent / aq. AcOH / 4 h / Heating 3.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 4.1: Et3N / 10 h / 20 °C 5.1: 71 percent / DIPEA; DMAP / CH2Cl2 / 6 h / 20 °C 6.1: 94 percent / H2 / Pd(OH)2/C / ethyl acetate / 12 h 7.1: LDA / tetrahydrofuran / 1 h / -50 °C 7.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -50 - 0 °C 8.1: LiOH; H2O / tetrahydrofuran; methanol / 12 h / 0 - 20 °C 9.1: 210 mg / PhSO2Cl; pyridine / 12 h / 0 °C 10.1: 88 percent / BF3*Et2O; ethane-1,2-dithiol / CH2Cl2 / 1 h / 0 °C View Scheme
参考文献
Synthesis, , # 22 p. 3888 - 3894
反应条件
1.1: 72 percent / aq. AcOH / 4 h / Heating 2.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 3.1: Et3N / 10 h / 20 °C 4.1: 71 percent / DIPEA; DMAP / CH2Cl2 / 6 h / 20 °C 5.1: 94 percent / H2 / Pd(OH)2/C / ethyl acetate / 12 h 6.1: LDA / tetrahydrofuran / 1 h / -50 °C 6.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -50 - 0 °C 7.1: LiOH; H2O / tetrahydrofuran; methanol / 12 h / 0 - 20 °C 8.1: 210 mg / PhSO2Cl; pyridine / 12 h / 0 °C 9.1: 88 percent / BF3*Et2O; ethane-1,2-dithiol / CH2Cl2 / 1 h / 0 °C View Scheme
参考文献
Synthesis, , # 22 p. 3888 - 3894
反应条件
1.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 2.1: Et3N / 10 h / 20 °C 3.1: 71 percent / DIPEA; DMAP / CH2Cl2 / 6 h / 20 °C 4.1: 94 percent / H2 / Pd(OH)2/C / ethyl acetate / 12 h 5.1: LDA / tetrahydrofuran / 1 h / -50 °C 5.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -50 - 0 °C 6.1: LiOH; H2O / tetrahydrofuran; methanol / 12 h / 0 - 20 °C 7.1: 210 mg / PhSO2Cl; pyridine / 12 h / 0 °C 8.1: 88 percent / BF3*Et2O; ethane-1,2-dithiol / CH2Cl2 / 1 h / 0 °C View Scheme
参考文献
Synthesis, , # 22 p. 3888 - 3894
