(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
1.1: 98 percent / 4 N HCl / tetrahydrofuran / 23 °C 2.1: 60 percent / aq. CsCO3 / methanol; dimethylformamide / 23 °C 3.1: Me4NB(OAc)3H / acetic acid; acetonitrile / 24 h / -40 °C 3.2: 96 percent / 2,6-lutidine / CH2Cl2 / 2.5 h / -78 °C 4.1: 99 percent / H2 / Pd(OH)2 / ethyl acetate; methanol / 23 °C 5.1: 74 percent / PhSO2Cl; pyridine / 48 h / 0 °C 6.1: 70 percent / TBAF; AcOH / tetrahydrofuran / 4 h / 0 °C View Scheme
参考文献
Organic letters, , vol. 2, # 16 p. 2405 - 2407
反应条件
1.1: 77 percent / CAN; HNO3 / ethanol / -45 °C 2.1: 98 percent / 4 N HCl / tetrahydrofuran / 23 °C 3.1: 60 percent / aq. CsCO3 / methanol; dimethylformamide / 23 °C 4.1: Me4NB(OAc)3H / acetic acid; acetonitrile / 24 h / -40 °C 4.2: 96 percent / 2,6-lutidine / CH2Cl2 / 2.5 h / -78 °C 5.1: 99 percent / H2 / Pd(OH)2 / ethyl acetate; methanol / 23 °C 6.1: 74 percent / PhSO2Cl; pyridine / 48 h / 0 °C 7.1: 70 percent / TBAF; AcOH / tetrahydrofuran / 4 h / 0 °C View Scheme
参考文献
Organic letters, , vol. 2, # 16 p. 2405 - 2407
反应条件
1.1: 80 percent / DCC; CuCl / acetonitrile / 18 h / 60 °C 2.1: 50 percent / Zn; AcOH / tetrahydrofuran / 0.25 h / 0 °C 3.1: 77 percent / CAN; HNO3 / ethanol / -45 °C 4.1: 98 percent / 4 N HCl / tetrahydrofuran / 23 °C 5.1: 60 percent / aq. CsCO3 / methanol; dimethylformamide / 23 °C 6.1: Me4NB(OAc)3H / acetic acid; acetonitrile / 24 h / -40 °C 6.2: 96 percent / 2,6-lutidine / CH2Cl2 / 2.5 h / -78 °C 7.1: 99 percent / H2 / Pd(OH)2 / ethyl acetate; methanol / 23 °C 8.1: 74 percent / PhSO2Cl; pyridine / 48 h / 0 °C 9.1: 70 percent / TBAF; AcOH / tetrahydrofuran / 4 h / 0 °C View Scheme
参考文献
Organic letters, , vol. 2, # 16 p. 2405 - 2407
反应条件
1.1: Me4NB(OAc)3H / acetic acid; acetonitrile / 24 h / -40 °C 1.2: 96 percent / 2,6-lutidine / CH2Cl2 / 2.5 h / -78 °C 2.1: 99 percent / H2 / Pd(OH)2 / ethyl acetate; methanol / 23 °C 3.1: 74 percent / PhSO2Cl; pyridine / 48 h / 0 °C 4.1: 70 percent / TBAF; AcOH / tetrahydrofuran / 4 h / 0 °C View Scheme
参考文献
Organic letters, , vol. 2, # 16 p. 2405 - 2407
反应条件
1: 99 percent / H2 / Pd(OH)2 / ethyl acetate; methanol / 23 °C 2: 74 percent / PhSO2Cl; pyridine / 48 h / 0 °C 3: 70 percent / TBAF; AcOH / tetrahydrofuran / 4 h / 0 °C View Scheme
参考文献
Organic letters, , vol. 2, # 16 p. 2405 - 2407
反应条件
1: 1.) LDA / 1.) THF, -50 deg C, 40 min; -30 deg C, 40 min, 2.) HMPA, -50 deg C, 1 h; -20 deg C, 2 h; 0 deg C, 1 h 2: 1 N KOH / ethanol / 4 h / 50 °C 3: benzenesulfonyl chloride, pyridine / 0 °C 4: H2 / 10percent Pd-C / ethyl acetate View Scheme
参考文献
Journal of Organic Chemistry, , vol. 58, # 27 p. 7768 - 7781
反应条件
1: 78 percent / trifluoromethansulfonic acid / CH2Cl2; cyclohexane / 3.5 h / Ambient temperature 2: 82 percent / DIBAH / CH2Cl2 / 0.5 h / -78 °C 3: TiCl4 / CH2Cl2 / 1.5 h / -78 °C 4: 64 percent / KOH/MeOH / 3 h / Heating 5: 61 percent / benzenesulfonyl chloride / pyridine / 24 h / 0 °C 6: 70 percent / hydrogen / Pd/C (10percent) / tetrahydrofuran / Ambient temperature View Scheme
参考文献
Helvetica Chimica Acta, , vol. 70, # 5 p. 1412 - 1418
反应条件
1: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C 2: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h 3: 73 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / -10 - 20 °C 4: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature 5: benzenesulfonylchloride, pyridine / 0 °C 6: 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: 57 percent / I2, Cu / 48 h / 70 °C 2: 83 percent / 1.8M EtAlCl2 / toluene; diethyl ether / -40 - 0 °C 3: H2 / 10percent Pd-C / tetrahydrofuran / 8 h / Ambient temperature 4: 71 percent / TBAF*3H2O / tetrahydrofuran / 0.17 h / -90 °C View Scheme
参考文献
Synthesis, , # SPEC. ISS. p. 1294 - 1300
反应条件
1: ZnCl2 / CH2Cl2 / 60 h / 20 °C 2: 190 mg / aq. HF / acetonitrile / 7 h / 0 - 23 °C View Scheme
参考文献
Organic Letters, , vol. 8, # 20 p. 4497 - 4500
