5-((叔丁基二甲基甲硅烷基)氧基)戊醛合成路线 （共 30 条）
反应条件
1: With sodium hydrogencarbonate; ozone in methanol; dichloromethane
T=-78°C; 3.5 h;
2: With dimethylsulfide in methanol; dichloromethane
T=-78 - 20°C;
参考文献
Krishnan, Shyam; Schreiber, Stuart L.
Organic Letters, 2004 , vol. 6, # 22 p. 4021 - 4024
反应条件
1: imidazole / dimethylformamide
2: 1.) O3, 2.) Ph3P / 1.) -78 deg C
View Scheme
参考文献
Brosius, Arthur D.; Overman, Larry E.; Schwink, Lothar
Journal of the American Chemical Society, 1999 , vol. 121, # 4 p. 700 - 709
反应条件
0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; triethylamine; pyridinium chlorochromate
1.) CH2Cl2, 2.) CH2Cl2; Multistep reaction;
参考文献
Danishefsky, Samuel J.; Pearson, William H.
Journal of Organic Chemistry, 1983 , vol. 48, # 21 p. 3865 - 3866
反应条件
water; silica gel in diethyl ether; benzene-d6
参考文献
Zhang, Zhe; Schafer, Laurel L.
Organic Letters, 2003 , vol. 5, # 24 p. 4733 - 4736
反应条件
1.1: 99 percent / imidazole; 4-DMAP / dimethylformamide / 6 h / 20 °C
2.1: NaHCO3; O3 / CH2Cl2; methanol / 3.5 h / -78 °C
2.2: 9.4 g / Me2S / CH2Cl2; methanol / -78 - 20 °C
View Scheme
参考文献
Krishnan, Shyam; Schreiber, Stuart L.
Organic Letters, 2004 , vol. 6, # 22 p. 4021 - 4024
反应条件
1: Zn; 1,2-diiodoethane / tetrahydrofuran / sonication
2: NaH / tetrahydrofuran
3: aq. HCl / tetrahydrofuran
4: 100 percent Chromat. / AgSbF5 / Ph3AuCl / CH2Cl2; H2O / 24 h / 35 °C
View Scheme
参考文献
Jung, Hyung Hoon; Floreancig, Paul E.
Organic Letters, 2006 , vol. 8, # 9 p. 1949 - 1951
反应条件
in diethyl ether
Inert atmosphere;
参考文献
Liu, Lei; Floreancig, Paul E.
Organic Letters, 2009 , vol. 11, # 14 p. 3152 - 3155
反应条件
in tetrahydrofuran; diethyl ether
T=-78°C; 0.166667 h;
参考文献
Allegretti, Paul A.; Ferreira, Eric M.
Journal of the American Chemical Society, 2013 , vol. 135, # 46 p. 17266 - 17269
反应条件
1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 96 percent / tetrahydrofuran; hexane / 0.17 h / -78 °C
2.1: 1.03 g / N,N-dimethylaminoethanol / 8 h / 80 °C
3.1: 69 percent / Et3N; trichlorosilane / benzene / 0.17 h / 20 °C
4.1: Co2(CO)8 / CH2Cl2 / 0.5 h / 0 °C
4.2: BF3*Et2O / CH2Cl2 / 0.17 h / -78 - 0 °C
4.3: 74 percent / CAN / methanol / 0.5 h / 0 °C
5.1: K2CO3 / methanol / 1 h / 20 °C
View Scheme
参考文献
Mukai, Chisato; Sugimoto, Yu-Ichi; Ikeda, Yoshitaka; Hanaoka, Miyoji
Tetrahedron, 1998 , vol. 54, # 5-6 p. 823 - 850
反应条件
1.1: N,N-diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C
1.2: 34 percent / tetrahydrofuran; hexane / 16 h / 20 °C
2.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C
3.1: 79 percent / Ph3P; imidazole; iodine / tetrahydrofuran / 2 h / 20 °C
View Scheme
参考文献
Dressel, Martina; Aechtner, Tobias; Bach, Thorsten
Synthesis, 2006 , # 13 p. 2206 - 2214
