(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
1.1: 89 percent / MeLi / tetrahydrofuran / 0.33 h / -78 °C 2.1: 82 percent / p-TsOH / CH2Cl2 / 2 h / 20 °C 3.1: 90 percent / Bu4NF / tetrahydrofuran / 12 h / 20 °C 4.1: NaH; 15-crown-5 / tetrahydrofuran / 14 h / Heating 4.2: 93 percent / Bu4NF / tetrahydrofuran 5.1: 59 percent / (PhO)2P(O)N3; DIAD; PPh3 / toluene / 12 h / 20 °C 6.1: 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: t-BuLi / tetrahydrofuran; diethyl ether / 0.08 h / -78 °C 1.2: CuBr*SMe2 / diethyl ether; various solvent(s) / 12 h / -40 - 20 °C 1.3: H2O 2.1: 82 percent / p-TsOH / CH2Cl2 / 2 h / 20 °C 3.1: 90 percent / Bu4NF / tetrahydrofuran / 12 h / 20 °C 4.1: NaH; 15-crown-5 / tetrahydrofuran / 14 h / Heating 4.2: 93 percent / Bu4NF / tetrahydrofuran 5.1: 59 percent / (PhO)2P(O)N3; DIAD; PPh3 / toluene / 12 h / 20 °C 6.1: 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: NaH; 15-crown-5 / tetrahydrofuran / 14 h / Heating 1.2: 93 percent / Bu4NF / tetrahydrofuran 2.1: 59 percent / (PhO)2P(O)N3; DIAD; PPh3 / toluene / 12 h / 20 °C 3.1: 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: 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
反应条件
1.1: 90 percent / Bu4NF / tetrahydrofuran / 12 h / 20 °C 2.1: NaH; 15-crown-5 / tetrahydrofuran / 14 h / Heating 2.2: 93 percent / Bu4NF / tetrahydrofuran 3.1: 59 percent / (PhO)2P(O)N3; DIAD; PPh3 / toluene / 12 h / 20 °C 4.1: 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: PhLi / toluene / 0.75 h / -25 °C 1.2: 44 percent / toluene; tetrahydrofuran / 0.33 h / -25 °C 2.1: 86 percent / TEA / CH2Cl2 / 0.67 h 3.1: 21 percent / NaN3 / dimethylsulfoxide / 72 h / Heating 4.1: 96 percent / p-TsOH*H2O / CH2Cl2; methanol / 14 h View Scheme
参考文献
Chemistry and Physics of Lipids, , vol. 111, # 2 p. 111 - 138
反应条件
1: 91 percent / NEt3, DMAP / CH2Cl2 2: NEt3, DMAP / CH2Cl2 / 0 °C 3: NaN3 / 18-crown-6 / dimethylformamide / 20 h / 75 °C 4: 87 percent / DDQ, H2O / CH2Cl2 / 2 h / 0 °C 5: 94 percent / Bu4NF*3H2O / tetrahydrofuran / 1 h View Scheme
参考文献
Tetrahedron, , vol. 49, # 30 p. 6645 - 6650
反应条件
1: 93 percent / 2percent aq. H2SO4 / methanol / Ambient temperature 2: 91 percent / NEt3, DMAP / CH2Cl2 3: NEt3, DMAP / CH2Cl2 / 0 °C 4: NaN3 / 18-crown-6 / dimethylformamide / 20 h / 75 °C 5: 87 percent / DDQ, H2O / CH2Cl2 / 2 h / 0 °C 6: 94 percent / Bu4NF*3H2O / tetrahydrofuran / 1 h View Scheme
参考文献
Tetrahedron, , vol. 49, # 30 p. 6645 - 6650
反应条件
1: NEt3, DMAP / CH2Cl2 / 0 °C 2: NaN3 / 18-crown-6 / dimethylformamide / 20 h / 75 °C 3: 87 percent / DDQ, H2O / CH2Cl2 / 2 h / 0 °C 4: 94 percent / Bu4NF*3H2O / tetrahydrofuran / 1 h View Scheme
参考文献
Tetrahedron, , vol. 49, # 30 p. 6645 - 6650
反应条件
1: NaN3 / 18-crown-6 / dimethylformamide / 20 h / 75 °C 2: 87 percent / DDQ, H2O / CH2Cl2 / 2 h / 0 °C 3: 94 percent / Bu4NF*3H2O / tetrahydrofuran / 1 h View Scheme
参考文献
Tetrahedron, , vol. 49, # 30 p. 6645 - 6650
