(2S,3R,4E)-2-叠氮-4-十八碳烯-1,3-二醇合成路线 （共 62 条）
反应条件
toluene-4-sulfonic acid in methanol; dichloromethane 12 h; Ambient temperature;
参考文献
Zimmermann, Peter; Schmidt, Richard R.
Liebigs Annalen der Chemie, 1988 , p. 663 - 668
反应条件
1: 1.) (nBu)2BOTf, Et3N, 4.) H2O2 / 1.) -78 deg C, 30 min, 2.) 20 deg C, 2 h, 3.) 0 deg C, 2 h, 4.) MeOH, ether, 0 deg C, 1 h 2: 92 percent / NaN3 / dimethylsulfoxide / 12 h / 25 °C 3: 97 percent / 2,6-lutidine / CH2Cl2 / 2.5 h / 0 °C 4: 81 percent / LiBH4 / tetrahydrofuran / 3 h / 0 °C 5: 90 percent / nBu4NF / tetrahydrofuran / 1 h / 25 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 110, # 23 p. 7910 - 7912
反应条件
1: 97 percent / 2,6-lutidine / CH2Cl2 / 2.5 h / 0 °C 2: 81 percent / LiBH4 / tetrahydrofuran / 3 h / 0 °C 3: 90 percent / nBu4NF / tetrahydrofuran / 1 h / 25 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 110, # 23 p. 7910 - 7912
反应条件
1: 81 percent / LiBH4 / tetrahydrofuran / 3 h / 0 °C 2: 90 percent / nBu4NF / tetrahydrofuran / 1 h / 25 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 110, # 23 p. 7910 - 7912
反应条件
1: 92 percent / NaN3 / dimethylsulfoxide / 12 h / 25 °C 2: 97 percent / 2,6-lutidine / CH2Cl2 / 2.5 h / 0 °C 3: 81 percent / LiBH4 / tetrahydrofuran / 3 h / 0 °C 4: 90 percent / nBu4NF / tetrahydrofuran / 1 h / 25 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 110, # 23 p. 7910 - 7912
反应条件
1: With tetra-(n-butyl)ammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene in toluene 2 h; Heating; 2: With hydrogenchloride in toluene T=20°C; 2 h;
参考文献
Kim, Sanghee; Lee, Sukjin; Lee, Taeho; Ko, Hyojin; Kim, Deukjoon
Journal of Organic Chemistry, 2006 , vol. 71, # 22 p. 8661 - 8664
反应条件
1.1: 80 percent / mCPBA; NaHCO3 / CH2Cl2 / 12 h / 0 - 20 °C 2.1: 89 percent / MeLi / tetrahydrofuran / 0.33 h / -78 °C 3.1: 82 percent / p-TsOH / CH2Cl2 / 2 h / 20 °C 4.1: 90 percent / Bu4NF / tetrahydrofuran / 12 h / 20 °C 5.1: NaH; 15-crown-5 / tetrahydrofuran / 14 h / Heating 5.2: 93 percent / Bu4NF / tetrahydrofuran 6.1: 59 percent / (PhO)2P(O)N3; DIAD; PPh3 / toluene / 12 h / 20 °C 7.1: 82 percent / p-TsOH / methanol / 12 h / 20 °C View Scheme
参考文献
Chemical communications (Cambridge, England), , # 5 p. 426 - 427
反应条件
1.1: trifluoromethanesulfonyl azide; potassium carbonate; copper(II) sulfate / methanol; H2O; CH2Cl2 / 3 h / 20 °C 2.1: 87 percent / triethylamine; 4-dimethylaminopyridine / CH2Cl2; dimethylformamide / 24 h / 20 °C 3.1: thionyl chloride; triethylamine / CH2Cl2 / 0.5 h / 0 °C 4.1: 1.09 g / sodium periodate; ruthenium(III) chloride trihydrate / CCl4; acetonitrile; H2O / 2 h / 20 °C 5.1: tetrabutylammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 2 h / Heating 5.2: 87 percent / sulfuric acid / toluene; tetrahydrofuran; H2O / 1 h / 20 °C 6.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 71, # 22 p. 8661 - 8664
反应条件
1.1: 87 percent / triethylamine; 4-dimethylaminopyridine / CH2Cl2; dimethylformamide / 24 h / 20 °C 2.1: thionyl chloride; triethylamine / CH2Cl2 / 0.5 h / 0 °C 3.1: 1.09 g / sodium periodate; ruthenium(III) chloride trihydrate / CCl4; acetonitrile; H2O / 2 h / 20 °C 4.1: tetrabutylammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 2 h / Heating 4.2: 87 percent / sulfuric acid / toluene; tetrahydrofuran; H2O / 1 h / 20 °C 5.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 71, # 22 p. 8661 - 8664
反应条件
1.1: 82 percent / p-TsOH / CH2Cl2 / 2 h / 20 °C 2.1: 90 percent / Bu4NF / tetrahydrofuran / 12 h / 20 °C 3.1: NaH; 15-crown-5 / tetrahydrofuran / 14 h / Heating 3.2: 93 percent / Bu4NF / tetrahydrofuran 4.1: 59 percent / (PhO)2P(O)N3; DIAD; PPh3 / toluene / 12 h / 20 °C 5.1: 82 percent / p-TsOH / methanol / 12 h / 20 °C View Scheme
参考文献
Chemical communications (Cambridge, England), , # 5 p. 426 - 427
