(3R,4s,5r)-4-羟基-5-[(1s)-1-羟基-2-甲基丙基]-3-甲基-2-吡咯烷酮-5-羧酸合成路线 （共 96 条）
反应条件
bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine in dichloromethane T=20°C; 3 h;
参考文献
Ooi, Hidenori; Ishibashi, Norihisa; Iwabuchi, Yoshiharu; Ishihara, Jun; Hatakeyama, Susumi
Journal of Organic Chemistry, 2004 , vol. 69, # 22 p. 7765 - 7768
反应条件
sodium hydroxide
T=4°C; Hydrolysis; 20 h;
参考文献
Soucy, Francois; Grenier, Louis; Behnke, Mark L.; Destree, Antonia T.; McCormack, Teresa A.; Adams, Julian; Plamondon, Louis
Journal of the American Chemical Society, 1999 , vol. 121, # 43 p. 9967 - 9976
反应条件
1.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexane / 0.75 h / -78.8 °C
1.2: dimethylaluminum chloride / tetrahydrofuran; hexane / 1 h / -78.8 °C
1.3: tetrahydrofuran; hexane / -85 - -20 °C
2.1: H2; 20 percent Pd(OH)2/C / methanol; acetic acid / 75 h / 20 °C / 2585.74 Torr
3.1: 93 percent / 0.6 N aq. NaOH / 20 h / 4 °C
View Scheme
参考文献
Soucy, Francois; Grenier, Louis; Behnke, Mark L.; Destree, Antonia T.; McCormack, Teresa A.; Adams, Julian; Plamondon, Louis
Journal of the American Chemical Society, 1999 , vol. 121, # 43 p. 9967 - 9976
反应条件
1: 60 percent / TiCl4 / -78 - 35 °C
2: O3; Me2S
3: NaClO2; NaH2PO4
4: HCOONH4 / Pd black
5: NaOH; H2O
View Scheme
参考文献
Panek, James S.; Masse, Craig E.
Angewandte Chemie - International Edition, 1999 , vol. 38, # 8 p. 1093 - 1095
反应条件
1: dicyclohexylcarbodiimide; DMSO; CF3COOH / pyridine
2: 60 percent / TiCl4 / -78 - 35 °C
3: O3; Me2S
4: NaClO2; NaH2PO4
5: HCOONH4 / Pd black
6: NaOH; H2O
View Scheme
参考文献
Panek, James S.; Masse, Craig E.
Angewandte Chemie - International Edition, 1999 , vol. 38, # 8 p. 1093 - 1095
反应条件
sodium hydroxide
Ambient temperature;
参考文献
Uno, Hidemitsu; Baldwin, Jack E.; Russell, Andrew T.
Journal of the American Chemical Society, 1994 , vol. 116, # 5 p. 2139 - 2140
反应条件
1: 85 percent / TsOH / 1,2-dimethoxy-ethane / 4 h
2: 85 percent / LHMDS / tetrahydrofuran / -78 °C
3: dicyclohexylcarbodiimide; DMSO; CF3COOH / pyridine
4: 60 percent / TiCl4 / -78 - 35 °C
5: O3; Me2S
6: NaClO2; NaH2PO4
7: HCOONH4 / Pd black
8: NaOH; H2O
View Scheme
参考文献
Panek, James S.; Masse, Craig E.
Angewandte Chemie - International Edition, 1999 , vol. 38, # 8 p. 1093 - 1095
反应条件
1: 1.) O3, 2.) Me2S / 1.) MeOH, CH2Cl2, -78 deg C, 2.) MeOH, a) -78 deg C, 1 h, b) RT, 1 h
2: 91 percent / ammonium formate, AcOH / Pd / 4 h / Heating
3: 90 percent / 0.1 N NaOH / ethanol / 9 h / Ambient temperature
View Scheme
参考文献
Nagamitsu, Tohru; Sunazuka, Toshiaki; Tanaka, Haruo; Omura, Satoshi; Sprengeler, Paul A.; Smith III, Amos B.
Journal of the American Chemical Society, 1996 , vol. 118, # 15 p. 3584 - 3590
反应条件
1: 80 percent / tetrahydrofuran / 24 h / -20 °C
View Scheme
参考文献
Corey, E. J.; Reichard, Gregory, A.; Kania, Robert
Tetrahedron Letters, 1993 , vol. 34, # 44 p. 6977 - 6980
反应条件
sodium methylate in methanol
T=20°C;
参考文献
Hayes, Christopher J.; Sherlock, Alexandra E.; Selby, Matthew D.
Organic and Biomolecular Chemistry, 2006 , vol. 4, # 2 p. 193 - 195
