(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.) c-Hex2BCl, Me2NEt 3.) H2O2, NaOH / 1.) Et2O, 0 deg C, 2 h, 2.) - 78 deg C, 4 h, 3.) MeOH, 0 deg C, 2 h 2: 82 percent / LiAlH4 / diethyl ether / 0.5 h / -78 deg C to 20 deg C 3: 100 percent / Pb(OAc)4, Na2CO3 / CH2Cl2 / 1 h / 0 °C 4: 100 percent / NaClO2, Na2H2PO4, 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 24 h 5: PhSO2Cl, py / 1.) 0 deg C, 10 min, 2.) 4 deg C, 24 h 6: H2 / Pd/C / ethyl acetate / 4 h / 20 °C View Scheme
参考文献
Tetrahedron Letters, , vol. 40, # 2 p. 393 - 394
反应条件
1: 100 percent / Pb(OAc)4, Na2CO3 / CH2Cl2 / 1 h / 0 °C 2: 100 percent / NaClO2, Na2H2PO4, 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 24 h 3: PhSO2Cl, py / 1.) 0 deg C, 10 min, 2.) 4 deg C, 24 h 4: H2 / Pd/C / ethyl acetate / 4 h / 20 °C View Scheme
参考文献
Tetrahedron Letters, , vol. 40, # 2 p. 393 - 394
反应条件
1: 82 percent / LiAlH4 / diethyl ether / 0.5 h / -78 deg C to 20 deg C 2: 100 percent / Pb(OAc)4, Na2CO3 / CH2Cl2 / 1 h / 0 °C 3: 100 percent / NaClO2, Na2H2PO4, 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 24 h 4: PhSO2Cl, py / 1.) 0 deg C, 10 min, 2.) 4 deg C, 24 h 5: H2 / Pd/C / ethyl acetate / 4 h / 20 °C View Scheme
参考文献
Tetrahedron Letters, , vol. 40, # 2 p. 393 - 394
反应条件
1: 80 °C / 0.5 Torr 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: 43 percent / 1M TBAF*3H2O / tetrahydrofuran / 0.08 h / -80 °C 2: H2 / 10percent Pd-C / tetrahydrofuran View Scheme
参考文献
Synthesis, , # SPEC. ISS. p. 1294 - 1300
反应条件
1: HCl / 2 h / Ambient temperature 2: 0.1 eq. triflic acid / CH2Cl2; cyclohexane / 10 - 20 °C 3: 1.1 eq. DiBALH / CH2Cl2 / -78 °C 4: 83 percent / BF3*Et2O / diethyl ether / 3 h / -15 - 5 °C 5: 61 percent / 1.1 eq. TBAF / tetrahydrofuran / 0.02 h / 80 °C 6: 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: 1.4 eq. R-Alpine-Borane / neat (no solvent) / 8 h / 0 - 20 °C 2: 1) 2.4 eq. n-BuLi; 2) 1.4 M H2SO4 / 1) THF, -78 deg C; 2) from -20 deg C to room temperature 3: 1) 2 eq. dicyclohexylborane; 2) NaOH, H2O2 / 1) THF, 0 deg C; 2) 40-50 deg C 4: HCl / 2 h / Ambient temperature 5: 0.1 eq. triflic acid / CH2Cl2; cyclohexane / 10 - 20 °C 6: 1.1 eq. DiBALH / CH2Cl2 / -78 °C 7: 83 percent / BF3*Et2O / diethyl ether / 3 h / -15 - 5 °C 8: 61 percent / 1.1 eq. TBAF / tetrahydrofuran / 0.02 h / 80 °C 9: 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: 1) 2 eq. dicyclohexylborane; 2) NaOH, H2O2 / 1) THF, 0 deg C; 2) 40-50 deg C 2: HCl / 2 h / Ambient temperature 3: 0.1 eq. triflic acid / CH2Cl2; cyclohexane / 10 - 20 °C 4: 1.1 eq. DiBALH / CH2Cl2 / -78 °C 5: 83 percent / BF3*Et2O / diethyl ether / 3 h / -15 - 5 °C 6: 61 percent / 1.1 eq. TBAF / tetrahydrofuran / 0.02 h / 80 °C 7: 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: DIBAL-H 2: ZnCl2 / CH2Cl2 / 60 h / 20 °C 3: 190 mg / aq. HF / acetonitrile / 7 h / 0 - 23 °C View Scheme
参考文献
Organic Letters, , vol. 8, # 20 p. 4497 - 4500
反应条件
1: DIBAL-H 2: ZnCl2 / CH2Cl2 / 60 h / 20 °C 3: 190 mg / aq. HF / acetonitrile / 7 h / 0 - 23 °C View Scheme
参考文献
Organic Letters, , vol. 8, # 20 p. 4497 - 4500
