(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: 99 percent / Jones reagent / acetone / 0 °C 2: LiAlH4; (1R,2S)-(-)-N-methylephedrine; 2-ethylaminopyridine / diethyl ether / 3 h / -78 °C 3: 99 percent / 1N HCl / Heating 4: 70 percent / BH3; H2O2; NaOAc / tetrahydrofuran 5: 95 percent / LiOH View Scheme
参考文献
Organic letters, , vol. 3, # 2 p. 201 - 203
反应条件
1: LiAlH4; (1R,2S)-(-)-N-methylephedrine; 2-ethylaminopyridine / diethyl ether / 3 h / -78 °C 2: 99 percent / 1N HCl / Heating 3: 70 percent / BH3; H2O2; NaOAc / tetrahydrofuran 4: 95 percent / LiOH View Scheme
参考文献
Organic letters, , vol. 3, # 2 p. 201 - 203
反应条件
1: 70 percent / BH3; H2O2; NaOAc / tetrahydrofuran 2: 95 percent / LiOH View Scheme
参考文献
Organic letters, , vol. 3, # 2 p. 201 - 203
反应条件
1: 99 percent / 1N HCl / Heating 2: 70 percent / BH3; H2O2; NaOAc / tetrahydrofuran 3: 95 percent / LiOH View Scheme
参考文献
Organic letters, , vol. 3, # 2 p. 201 - 203
反应条件
1.1: (Ipc)2BH / tetrahydrofuran / -78 - -10 °C / Inert atmosphere 1.2: 24 h / 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 2 h / 20 °C / Inert atmosphere 3.2: 3 h / Inert atmosphere 4.1: tetrahydrofuran; methanol / 2.5 h / 20 °C / Inert atmosphere; Molecular sieve 5.1: sodium cyanoborohydride; acetic acid / tetrahydrofuran; methanol / 20 h / 20 °C / Inert atmosphere 6.1: boron tribromide / dichloromethane / 16 h / 0 °C / Reflux; Inert atmosphere View Scheme
参考文献
Organic Letters, , vol. 14, # 2 p. 596 - 599
反应条件
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 2 h / 20 °C / Inert atmosphere 2.2: 3 h / Inert atmosphere 3.1: tetrahydrofuran; methanol / 2.5 h / 20 °C / Inert atmosphere; Molecular sieve 4.1: sodium cyanoborohydride; acetic acid / tetrahydrofuran; methanol / 20 h / 20 °C / Inert atmosphere 5.1: boron tribromide / dichloromethane / 16 h / 0 °C / Reflux; Inert atmosphere View Scheme
参考文献
Organic Letters, , vol. 14, # 2 p. 596 - 599
反应条件
1.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 2 h / 20 °C / Inert atmosphere 1.2: 3 h / Inert atmosphere 2.1: tetrahydrofuran; methanol / 2.5 h / 20 °C / Inert atmosphere; Molecular sieve 3.1: sodium cyanoborohydride; acetic acid / tetrahydrofuran; methanol / 20 h / 20 °C / Inert atmosphere 4.1: boron tribromide / dichloromethane / 16 h / 0 °C / Reflux; Inert atmosphere View Scheme
参考文献
Organic Letters, , vol. 14, # 2 p. 596 - 599
反应条件
1.1: 60 percent / hydrogen chloride / methanol; dimethylformamide / 1 h / 20 °C 2.1: 72 percent / sodium hydride / dimethylformamide / 0.5 h 3.1: acetonitrile / Heating 3.2: 81 percent / tetrabutylammonium fluoride / acetonitrile; tetrahydrofuran / 1.5 h / Heating 4.1: LiAlH4 / diethyl ether / 1 h 5.1: 1.52 g / triethylamine / CHCl3 6.1: 1.30 g / pyridinium p-toluenesulfonate / methanol; CHCl3 / 1 h / Heating 7.1: trifluoroacetic acid / 0.08 h / 20 °C 8.1: H2 / 10 percent Pd/C / acetic acid; methanol / 760 Torr 8.2: 1 M hydrochloric acid View Scheme
参考文献
Canadian Journal of Chemistry, , vol. 80, # 8 p. 857 - 865
反应条件
1.1: 72 percent / sodium hydride / dimethylformamide / 0.5 h 2.1: acetonitrile / Heating 2.2: 81 percent / tetrabutylammonium fluoride / acetonitrile; tetrahydrofuran / 1.5 h / Heating 3.1: LiAlH4 / diethyl ether / 1 h 4.1: 1.52 g / triethylamine / CHCl3 5.1: 1.30 g / pyridinium p-toluenesulfonate / methanol; CHCl3 / 1 h / Heating 6.1: trifluoroacetic acid / 0.08 h / 20 °C 7.1: H2 / 10 percent Pd/C / acetic acid; methanol / 760 Torr 7.2: 1 M hydrochloric acid View Scheme
参考文献
Canadian Journal of Chemistry, , vol. 80, # 8 p. 857 - 865
反应条件
1.1: LiAlH4 / diethyl ether / 1 h 2.1: 1.52 g / triethylamine / CHCl3 3.1: 1.30 g / pyridinium p-toluenesulfonate / methanol; CHCl3 / 1 h / Heating 4.1: trifluoroacetic acid / 0.08 h / 20 °C 5.1: H2 / 10 percent Pd/C / acetic acid; methanol / 760 Torr 5.2: 1 M hydrochloric acid View Scheme
参考文献
Canadian Journal of Chemistry, , vol. 80, # 8 p. 857 - 865
