2-[(7-溴庚基)氧基]四氢-2H-吡喃合成路线 （共 23 条）
反应条件
in dimethyl sulfoxide
1.) 0 deg C, 3 h, 2.) RT, 12 h;
参考文献
Jayasuriya, Nimal; Bosak, Stanislav; Regen, Steven L.
Journal of the American Chemical Society, 1990 , vol. 112, # 15 p. 5844 - 5850
参考文献
Ishmuratov; Ishmuratova; Odinokov; Tolstikov
Chemistry of Natural Compounds, 1997 , vol. 33, # 1 p. 25 - 30
反应条件
1.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C
1.2: 87 percent / HMPA / tetrahydrofuran; hexane / 24 h / -78 °C
2.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 48 h / 20 °C
View Scheme
参考文献
Carballeira, Nestor M.; Montano, Nashbly; Padilla, Luis F.
Chemistry and Physics of Lipids, 2007 , vol. 145, # 1 p. 37 - 44
反应条件
1: 1.) BuLi, HMPA / 1.) THF, -30 deg C, 2.) THF, from -30 deg C to RT
2: 90.3 percent / 10 percent HCl / methanol / 2 h / Heating
3: 87.7 percent / SOCl2, pyridine / benzene / 50 °C
View Scheme
参考文献
Satoh, Mitsuru; Takeuchi, Naoki; Fujita, Takeshi; Yamazaki, Katsuya; Tobinaga, Seisho
Chemical and Pharmaceutical Bulletin, 1998 , vol. 46, # 10 p. 1501 - 1505
反应条件
1: 1.) BuLi, 3.) toluene-p-sulfonic acid / 1) hexane; 2) THF, hexane, HMPA, room temperature, 10 h; 3) methanol, reflux, 3 h
2: 97 percent / Lindlar catalyst, quinoline, cyclohexene, H2 / 3 h
3: 97 percent / bromine-triphenylphosphine, Br2 / CH2Cl2 / 1 h / 0 °C
View Scheme
参考文献
Martichonok, Valeri; Jones, J. Bryan
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995 , # 22 p. 2927 - 2930
反应条件
1.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.5 h / -60 °C
1.2: -20 - 20 °C
2.1: Jone's reagent / acetone / 0 - 4 °C
View Scheme
参考文献
Fu, Yu; Weng, Yue; Hong, Wen-Xu; Zhang, Qinghai
Synlett, 2011 , # 6 p. 809 - 812
反应条件
1: 66 percent / ethylene diamine / dimethylsulfoxide / 20 h / Ambient temperature
2: 80 percent / I2, morpholine / toluene / 20 h / 45 °C
View Scheme
参考文献
Bjoerkling, Fredrik; Norin, Torbjoern; Unelius, Rikard
Synthetic Communications, 1985 , vol. 15, # 6 p. 463 - 472
反应条件
1.1: 72 percent / dimethylsulfoxide / 12 h / 10 °C
2.1: EtMgBr / tetrahydrofuran / 3 h / 40 °C
2.2: CuCN / tetrahydrofuran / 18 h / 20 °C
3.1: 0.93 g / PTS / methanol / 20 h / 20 °C
4.1: 88 percent / H2; quinoline / Pd/BaSO4 / ethanol
5.1: 65 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
View Scheme
参考文献
Akakabe, Yoshihiko; Washizu, Kensuke; Matsui, Kenji; Kajiwara, Tadahiko
Bioscience, Biotechnology and Biochemistry, 2005 , vol. 69, # 7 p. 1348 - 1352
反应条件
1.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.5 h / -60 °C
1.2: -20 - 20 °C
2.1: Jone's reagent / acetone / 0 - 4 °C
3.1: sulfuric acid / 20 °C
View Scheme
参考文献
Fu, Yu; Weng, Yue; Hong, Wen-Xu; Zhang, Qinghai
Synlett, 2011 , # 6 p. 809 - 812
反应条件
1.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.5 h / -60 °C
1.2: -20 - 20 °C
2.1: Jone's reagent / acetone / 0 - 4 °C
3.1: sulfuric acid / 20 °C
4.1: hydrogen; ethylenediamine / ethanol; water
View Scheme
参考文献
Fu, Yu; Weng, Yue; Hong, Wen-Xu; Zhang, Qinghai
Synlett, 2011 , # 6 p. 809 - 812
