(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
1.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C 3.2: 12 h / 0 - 20 °C 4.1: Pd(OH)2/C; hydrogen / methanol 5.1: hydrogenchloride / water; methanol / 6 h View Scheme
参考文献
Organic and Biomolecular Chemistry, , vol. 10, # 14 p. 2760 - 2773
反应条件
1.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C 2.2: 12 h / 0 - 20 °C 3.1: Pd(OH)2/C; hydrogen / methanol 4.1: hydrogenchloride / water; methanol / 6 h View Scheme
参考文献
Organic and Biomolecular Chemistry, , vol. 10, # 14 p. 2760 - 2773
反应条件
1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C 1.2: 12 h / 0 - 20 °C 2.1: Pd(OH)2/C; hydrogen / methanol 3.1: hydrogenchloride / water; methanol / 6 h View Scheme
参考文献
Organic and Biomolecular Chemistry, , vol. 10, # 14 p. 2760 - 2773
反应条件
potassium hydroxide 3 h; Heating;
参考文献
Organic and Biomolecular Chemistry, , vol. 3, # 9 p. 1729 - 1737
反应条件
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.42 h / 0 °C / |Inert atmosphere 1.2: 7 h / 0 - 20 °C / |Inert atmosphere 2.1: palladium diacetate; p-benozquinone / dimethyl sulfoxide / 48 h / 40 °C / |Molecular sieve 3.1: sodium hydroxide / water; methanol / 0.5 h / 20 °C 4.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 5.1: sodium azide / N,N-dimethyl-formamide / 4 h / 100 °C 6.1: water; AD-mix-β / tert-butyl alcohol / 12 h / 0 °C 7.1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / dichloromethane / 1.5 h / 20 °C / |Inert atmosphere 8.1: hydrogen; 10 Pd/C / methanol / 24 h / 20 °C / 2068.65 Torr 9.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 0 - 20 °C / |Inert atmosphere 10.1: hydrogenchloride; methanol / water / 6 h / 20 °C 11.1: sodium periodate / water; methanol / 1 h / 0 °C 12.1: sodium tetrahydroborate / water; methanol / 0.5 h / 20 °C 12.2: 3 h / |Reflux 13.1: ammonia / water; methanol / 20 °C View Scheme
参考文献
Tetrahedron Asymmetry, , vol. 23, # 17 p. 1234 - 1237
反应条件
1.1: palladium diacetate; p-benozquinone / dimethyl sulfoxide / 48 h / 40 °C / |Molecular sieve 2.1: sodium hydroxide / water; methanol / 0.5 h / 20 °C 3.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 4 h / 100 °C 5.1: water; AD-mix-β / tert-butyl alcohol / 12 h / 0 °C 6.1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / dichloromethane / 1.5 h / 20 °C / |Inert atmosphere 7.1: hydrogen; 10 Pd/C / methanol / 24 h / 20 °C / 2068.65 Torr 8.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 0 - 20 °C / |Inert atmosphere 9.1: hydrogenchloride; methanol / water / 6 h / 20 °C 10.1: sodium periodate / water; methanol / 1 h / 0 °C 11.1: sodium tetrahydroborate / water; methanol / 0.5 h / 20 °C 11.2: 3 h / |Reflux 12.1: ammonia / water; methanol / 20 °C View Scheme
参考文献
Tetrahedron Asymmetry, , vol. 23, # 17 p. 1234 - 1237
反应条件
1.1: sodium hydroxide / water; methanol / 0.5 h / 20 °C 2.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 3.1: sodium azide / N,N-dimethyl-formamide / 4 h / 100 °C 4.1: water; AD-mix-β / tert-butyl alcohol / 12 h / 0 °C 5.1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / dichloromethane / 1.5 h / 20 °C / |Inert atmosphere 6.1: hydrogen; 10 Pd/C / methanol / 24 h / 20 °C / 2068.65 Torr 7.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 0 - 20 °C / |Inert atmosphere 8.1: hydrogenchloride; methanol / water / 6 h / 20 °C 9.1: sodium periodate / water; methanol / 1 h / 0 °C 10.1: sodium tetrahydroborate / water; methanol / 0.5 h / 20 °C 10.2: 3 h / |Reflux 11.1: ammonia / water; methanol / 20 °C View Scheme
参考文献
Tetrahedron Asymmetry, , vol. 23, # 17 p. 1234 - 1237
反应条件
1.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 2.1: sodium azide / N,N-dimethyl-formamide / 4 h / 100 °C 3.1: water; AD-mix-β / tert-butyl alcohol / 12 h / 0 °C 4.1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / dichloromethane / 1.5 h / 20 °C / |Inert atmosphere 5.1: hydrogen; 10 Pd/C / methanol / 24 h / 20 °C / 2068.65 Torr 6.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 0 - 20 °C / |Inert atmosphere 7.1: hydrogenchloride; methanol / water / 6 h / 20 °C 8.1: sodium periodate / water; methanol / 1 h / 0 °C 9.1: sodium tetrahydroborate / water; methanol / 0.5 h / 20 °C 9.2: 3 h / |Reflux 10.1: ammonia / water; methanol / 20 °C View Scheme
参考文献
Tetrahedron Asymmetry, , vol. 23, # 17 p. 1234 - 1237
反应条件
1.1: water; AD-mix-β / tert-butyl alcohol / 12 h / 0 °C 2.1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / dichloromethane / 1.5 h / 20 °C / |Inert atmosphere 3.1: hydrogen; 10 Pd/C / methanol / 24 h / 20 °C / 2068.65 Torr 4.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 0 - 20 °C / |Inert atmosphere 5.1: hydrogenchloride; methanol / water / 6 h / 20 °C 6.1: sodium periodate / water; methanol / 1 h / 0 °C 7.1: sodium tetrahydroborate / water; methanol / 0.5 h / 20 °C 7.2: 3 h / |Reflux 8.1: ammonia / water; methanol / 20 °C View Scheme
参考文献
Tetrahedron Asymmetry, , vol. 23, # 17 p. 1234 - 1237
反应条件
1.1: hydrogen; 10 Pd/C / methanol / 24 h / 20 °C / 2068.65 Torr 2.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 18 h / 0 - 20 °C / |Inert atmosphere 3.1: hydrogenchloride; methanol / water / 6 h / 20 °C 4.1: sodium periodate / water; methanol / 1 h / 0 °C 5.1: sodium tetrahydroborate / water; methanol / 0.5 h / 20 °C 5.2: 3 h / |Reflux 6.1: ammonia / water; methanol / 20 °C View Scheme
参考文献
Tetrahedron Asymmetry, , vol. 23, # 17 p. 1234 - 1237
