(3S)-3-[[叔丁基二甲基硅烷基]氧基]-戊烷二酸 1-甲基酯合成路线 （共 8 条）
反应条件
1: With (9S)-6'-methoxycinchonan-9-ol in dichloromethane
T=-40 - -35°C; 15 - 20 h;
2: With hydrogenchloride in tert-butyl methyl ether; water
pH=4 - 5; Product distribution / selectivity;
参考文献
TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.
Patent: WO2008/130638 A2, 2008 ;
Location in patent: Page/Page column 31 ;
反应条件
1: BuLi / tetrahydrofuran; hexane
2: H2 / Pd(OH)2/C / ethyl acetate / Ambient temperature
3: NaOMe
View Scheme
参考文献
Konoike; Araki
Journal of Organic Chemistry, 1994 , vol. 59, # 25 p. 7849 - 7854
反应条件
hydrogen; palladium on activated charcoal in diethyl ether
0.333333 h;
参考文献
Heathcock, Clayton H.; Hadley, Cheri R.; Rosen, Terry; Theisen, Peter D.; Hecker, Scott J.
Journal of Medicinal Chemistry, 1987 , vol. 30, # 10 p. 1858 - 1873
反应条件
1: 95 percent / KHCO3 / dimethylformamide / 42 h / Ambient temperature
2: NaOAc, N2O4 / CCl4 / 0 °C
3: H2 / 20percent Pd(OH)2/C / 1) dioxane, 75-80 deg C, 1 h, 2) ethyl acetate, 35 psi, 20 h
View Scheme
参考文献
Karanewsky, Donald S.; Malley, Mary F.; Gougoutas, Jack Z.
Journal of Organic Chemistry, 1991 , vol. 56, # 11 p. 3744 - 3747
反应条件
Novozym 435 in 2,2,4-trimethylpentane
T=35°C; 24 h; Enzymatic reaction; optical yield given as percent eeenantioselective reaction;
参考文献
Wang, Bo; Liu, Ji; Tang, Xiaoling; Cheng, Cheng; Gu, Jiali; Dai, Liyan; Yu, Hongwei
Tetrahedron Letters, 2010 , vol. 51, # 2 p. 309 - 312
反应条件
1: 91 percent / Et3N / diethyl ether / 18 h / Ambient temperature
View Scheme
参考文献
Novak, Lajos; Rohaly, Janos; Poppe, Laszlo; Hornyanszky, Gabor; Kolonits, Pal; et al.
Liebigs Annalen der Chemie, 1992 , # 2 p. 145 - 158
参考文献
Konoike; Araki
Journal of Organic Chemistry, 1994 , vol. 59, # 25 p. 7849 - 7854
反应条件
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
参考文献
Novak, Lajos; Rohaly, Janos; Poppe, Laszlo; Hornyanszky, Gabor; Kolonits, Pal; et al.
Liebigs Annalen der Chemie, 1992 , # 2 p. 145 - 158
