(3R,4R,5R)-5-(羟基甲基)哌啶-3,4-二醇盐酸盐合成路线 （共 76 条）
反应条件
1: 88 percent / Ac2O; silica gel 60 2: 53 percent / H2 / 10percent Pd/C / methanol / 16 h / 20 °C View Scheme
参考文献
Chemistry - A European Journal, , vol. 7, # 17 p. 3744 - 3747
反应条件
1: methanol / Ambient temperature 2: pyridine / Ambient temperature 3: DMAP / acetonitrile / 1 h / Ambient temperature 4: Bu3SnH, VAZO / toluene / 1 h / 100 °C 5: 1.) NaOMe, MeOH, 2.) 1N aq. HCl / 1.) RT, 2 h, 2.) MeOH, RT, overnight View Scheme
参考文献
Journal of the American Chemical Society, , vol. 120, # 13 p. 3007 - 3018
反应条件
1: 99 percent / imidazole; DMAP / CH2Cl2 / 3 h / 20 °C 2: 72 percent / oxone; aq. Na2EDTA; CF3COCH3 / NaHCO3 / acetonitrile / 0 °C 3: 74 percent / n-BuLi; CuCN; BF3*Et2O / diethyl ether; hexane / 2 h / -78 °C 4: OsO4; NaIO4 / ethanol; H2O / 24 h / 20 °C 5: 167 mg / NaBH4 / ethanol; H2O / 1 h / 20 °C 6: 99 percent / aq. HCl / dioxane / 1 h / Heating View Scheme
参考文献
Journal of Organic Chemistry, , vol. 70, # 13 p. 5207 - 5214
反应条件
1: 72 percent / oxone; aq. Na2EDTA; CF3COCH3 / NaHCO3 / acetonitrile / 0 °C 2: 74 percent / n-BuLi; CuCN; BF3*Et2O / diethyl ether; hexane / 2 h / -78 °C 3: OsO4; NaIO4 / ethanol; H2O / 24 h / 20 °C 4: 167 mg / NaBH4 / ethanol; H2O / 1 h / 20 °C 5: 99 percent / aq. HCl / dioxane / 1 h / Heating View Scheme
参考文献
Journal of Organic Chemistry, , vol. 70, # 13 p. 5207 - 5214
反应条件
1.1: 660 mg / CBr4; Ph3P / CH2Cl2 / 1 h / 0 - 20 °C 2.1: 65 percent / K2CO3; TBAI / acetonitrile / 96 h / Heating 3.1: 60 percent / 1,4-dicyanonaphthalene / propan-2-ol / 1.5 h / UV-irradiation 4.1: 9-BBN / tetrahydrofuran / 20 h / 20 °C 4.2: 45 percent / NaOH; aq. H2O2 / tetrahydrofuran / 4 h / 0 - 20 °C 5.1: 100 percent / aq. HCl / methanol / 1 h / 20 °C 6.1: 95 percent / H2 / 20 percent Pd(OH)2/C / ethanol / 10 h / 20 °C / 3878.61 Torr View Scheme
参考文献
Synthesis, , # 8 p. 1263 - 1267
反应条件
1.1: 65 percent / K2CO3; TBAI / acetonitrile / 96 h / Heating 2.1: 60 percent / 1,4-dicyanonaphthalene / propan-2-ol / 1.5 h / UV-irradiation 3.1: 9-BBN / tetrahydrofuran / 20 h / 20 °C 3.2: 45 percent / NaOH; aq. H2O2 / tetrahydrofuran / 4 h / 0 - 20 °C 4.1: 100 percent / aq. HCl / methanol / 1 h / 20 °C 5.1: 95 percent / H2 / 20 percent Pd(OH)2/C / ethanol / 10 h / 20 °C / 3878.61 Torr View Scheme
参考文献
Synthesis, , # 8 p. 1263 - 1267
反应条件
1.1: 85 percent / TBAF / tetrahydrofuran / 4 h / 0 - 20 °C 2.1: 660 mg / CBr4; Ph3P / CH2Cl2 / 1 h / 0 - 20 °C 3.1: 65 percent / K2CO3; TBAI / acetonitrile / 96 h / Heating 4.1: 60 percent / 1,4-dicyanonaphthalene / propan-2-ol / 1.5 h / UV-irradiation 5.1: 9-BBN / tetrahydrofuran / 20 h / 20 °C 5.2: 45 percent / NaOH; aq. H2O2 / tetrahydrofuran / 4 h / 0 - 20 °C 6.1: 100 percent / aq. HCl / methanol / 1 h / 20 °C 7.1: 95 percent / H2 / 20 percent Pd(OH)2/C / ethanol / 10 h / 20 °C / 3878.61 Torr View Scheme
参考文献
Synthesis, , # 8 p. 1263 - 1267
反应条件
1.1: 9-BBN / tetrahydrofuran / 20 h / 20 °C 1.2: 45 percent / NaOH; aq. H2O2 / tetrahydrofuran / 4 h / 0 - 20 °C 2.1: 100 percent / aq. HCl / methanol / 1 h / 20 °C 3.1: 95 percent / H2 / 20 percent Pd(OH)2/C / ethanol / 10 h / 20 °C / 3878.61 Torr View Scheme
参考文献
Synthesis, , # 8 p. 1263 - 1267
反应条件
1: 100 percent / aq. HCl / methanol / 1 h / 20 °C 2: 95 percent / H2 / 20 percent Pd(OH)2/C / ethanol / 10 h / 20 °C / 3878.61 Torr View Scheme
参考文献
Synthesis, , # 8 p. 1263 - 1267
反应条件
1.1: 60 percent / 1,4-dicyanonaphthalene / propan-2-ol / 1.5 h / UV-irradiation 2.1: 9-BBN / tetrahydrofuran / 20 h / 20 °C 2.2: 45 percent / NaOH; aq. H2O2 / tetrahydrofuran / 4 h / 0 - 20 °C 3.1: 100 percent / aq. HCl / methanol / 1 h / 20 °C 4.1: 95 percent / H2 / 20 percent Pd(OH)2/C / ethanol / 10 h / 20 °C / 3878.61 Torr View Scheme
参考文献
Synthesis, , # 8 p. 1263 - 1267
