(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: TiCl4 / CH2Cl2 / 1.5 h / -78 °C 2: 64 percent / KOH/MeOH / 3 h / Heating 3: 61 percent / benzenesulfonyl chloride / pyridine / 24 h / 0 °C 4: 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
1.1: sodium amide / tetrahydrofuran / 4 h / Heating 1.2: tetrahydrofuran / -78 °C 2.1: mCPBA / diethyl ether / 1 h / 20 °C 2.2: aq. HCl / tetrahydrofuran / 2 h / 20 °C 3.1: NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 24 h / 20 °C 4.1: 1.13 g / PhSO2Cl; pyridine 5.1: 99 percent / H2 / Pd/C View Scheme
参考文献
Organic Letters, , vol. 1, # 5 p. 753 - 755
反应条件
1.1: mCPBA / diethyl ether / 1 h / 20 °C 1.2: aq. HCl / tetrahydrofuran / 2 h / 20 °C 2.1: NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 24 h / 20 °C 3.1: 1.13 g / PhSO2Cl; pyridine 4.1: 99 percent / H2 / Pd/C View Scheme
参考文献
Organic Letters, , vol. 1, # 5 p. 753 - 755
反应条件
1: NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 24 h / 20 °C 2: 1.13 g / PhSO2Cl; pyridine 3: 99 percent / H2 / Pd/C View Scheme
参考文献
Organic Letters, , vol. 1, # 5 p. 753 - 755
反应条件
1.1: tetrahydrofuran / -78 °C 2.1: mCPBA / diethyl ether / 1 h / 20 °C 2.2: aq. HCl / tetrahydrofuran / 2 h / 20 °C 3.1: NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 24 h / 20 °C 4.1: 1.13 g / PhSO2Cl; pyridine 5.1: 99 percent / H2 / Pd/C View Scheme
参考文献
Organic Letters, , vol. 1, # 5 p. 753 - 755
反应条件
1.1: sodium amide / tetrahydrofuran / 4 h / Heating 1.2: tetrahydrofuran / -78 °C 2.1: mCPBA / diethyl ether / 1 h / 20 °C 2.2: aq. HCl / tetrahydrofuran / 2 h / 20 °C 3.1: NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 24 h / 20 °C 4.1: 1.13 g / PhSO2Cl; pyridine 5.1: 99 percent / H2 / Pd/C View Scheme
参考文献
Organic Letters, , vol. 1, # 5 p. 753 - 755
反应条件
1.1: 78 percent / Ti(OiPr)4; (S)-BINOL / -20 °C 2.1: O3; TPP / CH2Cl2 / -78 °C 2.2: 78 percent / CH2Cl2 / 20 °C 3.1: 84 percent / DIBAL-H / CH2Cl2 / 1 h / 0 - 20 °C 4.1: CH2Cl2 5.1: K2CO3 / methanol / 20 °C 6.1: 98 percent / DIPEA; DMAP / CH2Cl2 / 0 - 20 °C 7.1: 90 percent / Na; NH3 / tetrahydrofuran / 0.75 h 8.1: 95 percent / H2 / PtO2 / ethyl acetate / 1 h / 20 °C 9.1: 94 percent / NaH; TBAI / tetrahydrofuran / 0 - 20 °C 10.1: 92 percent / BF3*OEt2; ethane dithiol / CH2Cl2 / 1 h / 0 - 20 °C 11.1: TEMPO; BAIB / CH2Cl2 / 20 °C 12.1: NaClO2; NaH2PO4 13.1: 78 percent / PhSO2Cl; pyridine / 12 h / 0 °C 14.1: 91 percent / H2 / Pd(OH)2 / ethyl acetate / 12 h View Scheme
参考文献
Tetrahedron Letters, , vol. 47, # 29 p. 4995 - 4998
反应条件
1.1: 82 percent / TBAF / dimethylformamide / 24 h / 23 °C 2.1: 80 percent / DCC; CuCl / acetonitrile / 18 h / 60 °C 3.1: 50 percent / Zn; AcOH / tetrahydrofuran / 0.25 h / 0 °C 4.1: 77 percent / CAN; HNO3 / ethanol / -45 °C 5.1: 98 percent / 4 N HCl / tetrahydrofuran / 23 °C 6.1: 60 percent / aq. CsCO3 / methanol; dimethylformamide / 23 °C 7.1: Me4NB(OAc)3H / acetic acid; acetonitrile / 24 h / -40 °C 7.2: 96 percent / 2,6-lutidine / CH2Cl2 / 2.5 h / -78 °C 8.1: 99 percent / H2 / Pd(OH)2 / ethyl acetate; methanol / 23 °C 9.1: 74 percent / PhSO2Cl; pyridine / 48 h / 0 °C 10.1: 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: 82 percent / TBAF / dimethylformamide / 24 h / 23 °C 2.1: 80 percent / DCC; CuCl / acetonitrile / 18 h / 60 °C 3.1: 50 percent / Zn; AcOH / tetrahydrofuran / 0.25 h / 0 °C 4.1: 77 percent / CAN; HNO3 / ethanol / -45 °C 5.1: 98 percent / 4 N HCl / tetrahydrofuran / 23 °C 6.1: 60 percent / aq. CsCO3 / methanol; dimethylformamide / 23 °C 7.1: Me4NB(OAc)3H / acetic acid; acetonitrile / 24 h / -40 °C 7.2: 96 percent / 2,6-lutidine / CH2Cl2 / 2.5 h / -78 °C 8.1: 99 percent / H2 / Pd(OH)2 / ethyl acetate; methanol / 23 °C 9.1: 74 percent / PhSO2Cl; pyridine / 48 h / 0 °C 10.1: 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: 60 percent / aq. CsCO3 / methanol; dimethylformamide / 23 °C 2.1: Me4NB(OAc)3H / acetic acid; acetonitrile / 24 h / -40 °C 2.2: 96 percent / 2,6-lutidine / CH2Cl2 / 2.5 h / -78 °C 3.1: 99 percent / H2 / Pd(OH)2 / ethyl acetate; methanol / 23 °C 4.1: 74 percent / PhSO2Cl; pyridine / 48 h / 0 °C 5.1: 70 percent / TBAF; AcOH / tetrahydrofuran / 4 h / 0 °C View Scheme
参考文献
Organic letters, , vol. 2, # 16 p. 2405 - 2407
