alpha-酮戊二酸二甲酯合成路线 （共 32 条）
反应条件
copper(ll) bromide in chloroform; ethyl acetate 18 h; Heating;
参考文献
CHEMIZON, A DIVISION OF OPTOMAGIC CO., LTD.
Patent: US2012/238599 A1, 2012 ;
Location in patent: Page/Page column 32 ;
US 20120238599 A1
反应条件
1.1: Br2 / CH2Cl2 / 3 h / Heating
1.2: 3.6 mmol / Et3N / diethyl ether / 0.5 h
2.1: 16 percent / toluenesulfonic acid / CH2Cl2 / 24 h / Heating
View Scheme
参考文献
Carrigan, Christina N.; Bartlett, Richard D.; Esslinger, C. Sean; Cybulski, Kimberly A.; Tongcharoensirikul, Pakamas; Bridges, Richard J.; Thompson, Charles M.
Journal of Medicinal Chemistry, 2002 , vol. 45, # 11 p. 2260 - 2276
反应条件
1: Br2 / CH2Cl2 / Heating
2: Et3N / diethyl ether / 20 h / 25 °C
3: CH2Cl2 / 7 h / 25 °C
4: dry hydrogen chloride / CH2Cl2 / 10 h
5: 60 percent / ceric ammonium nitrate / acetonitrile; H2O / 0.17 h / 0 °C
6: 92 percent / p-tuluenesulfonic acid / methanol / 4 h / Heating
7: 98 percent / 0.5 M K2CO3 / H2O / 4 h / 85 °C
8: NH4OH / H2O / 30 h / 23 °C
View Scheme
参考文献
Corey,E.J.; Tramontano,A.
Journal of the American Chemical Society, 1981 , vol. 103, p. 5599
反应条件
1: Br2 / CH2Cl2 / Heating
2: Et3N / diethyl ether / 20 h / 25 °C
3: CH2Cl2 / 7 h / 25 °C
4: dry hydrogen chloride / CH2Cl2 / 10 h
5: 60 percent / ceric ammonium nitrate / acetonitrile; H2O / 0.17 h / 0 °C
View Scheme
参考文献
Corey,E.J.; Tramontano,A.
Journal of the American Chemical Society, 1981 , vol. 103, p. 5599
反应条件
1: 1.) Al, HgCl2 / 1.) 40 deg C, 2.) -78 deg C
2: aq. LiOH / tetrahydrofuran / Ambient temperature
3: 60 °C
4: 65 percent / N-methyl morpholine, 1-hydroxybenzotriazole, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / dimethylformamide / 12 h / Ambient temperature
5: PCC, molecular sieves 4 Angstroem / CH2Cl2 / 1.5 h / Ambient temperature
6: TFA, molecular sieves 4 Angstroem / CH2Cl2 / Ambient temperature
7: 1.) Bu3SnH, AIBN, 2.) TFA / 1.) PhMe, reflux, 2.) THF, r.t., 5 h
8: 1.) O3 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 2.) -78 deg C to r.t.
9: Et3N / tetrahydrofuran / 2 h / 60 °C
10: 67 percent / (Bu3Sn)2O / benzene / 72 h / Heating
View Scheme
参考文献
Clive, Derrick L. J.; Zhou, Yuanxi; De Lima, Denis Pires
Chemical Communications, 1996 , # 12 p. 1463 - 1464
反应条件
1: Br2 / CH2Cl2 / Heating
2: Et3N / diethyl ether / 20 h / 25 °C
View Scheme
参考文献
Corey,E.J.; Tramontano,A.
Journal of the American Chemical Society, 1981 , vol. 103, p. 5599
反应条件
baker's yeast
Ambient temperature; Yields of byproduct given;
参考文献
Drioli, Sara; Nitti, Patrizia; Pitacco, Giuliana; Tossut, Laura; Valentin, Ennio
Tetrahedron Asymmetry, 1999 , vol. 10, # 14 p. 2713 - 2728
反应条件
1.1: sodium hydride / tetrahydrofuran / |Cooling with ice
1.2: 0.5 h / |Cooling with ice
2.1: potassium hydroxide / ethanol; water / 1 h / |Reflux
2.2: pH 2
View Scheme
参考文献
Kang, Sunyoung; Kim, Youngeun; Song, Youngjun; Choi, Jin Uk; Park, Euddeum; Choi, Wonmin; Park, Jeongseon; Lee, Yan
Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 10 p. 2364 - 2367
反应条件
1: 2-(Diethoxy-phosphoryl)-propionic acid ethyl ester With sodium hydride in tetrahydrofuran
Cooling with ice;
2: α-ketoglutaric acid dimethyl ester in tetrahydrofuran
0.5 h; Cooling with ice;
参考文献
Kang, Sunyoung; Kim, Youngeun; Song, Youngjun; Choi, Jin Uk; Park, Euddeum; Choi, Wonmin; Park, Jeongseon; Lee, Yan
Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 10 p. 2364 - 2367
反应条件
1.1: Br2 / CH2Cl2 / 3 h / Heating
1.2: 3.6 mmol / Et3N / diethyl ether / 0.5 h
2.1: 40 percent / toluenesulfonic acid / CH2Cl2 / 24 h / Heating
3.1: 43 percent / aq. OH- / tetrahydrofuran
View Scheme
参考文献
Carrigan, Christina N.; Bartlett, Richard D.; Esslinger, C. Sean; Cybulski, Kimberly A.; Tongcharoensirikul, Pakamas; Bridges, Richard J.; Thompson, Charles M.
Journal of Medicinal Chemistry, 2002 , vol. 45, # 11 p. 2260 - 2276
