(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
1.1: BF3*OEt2 / CH2Cl2 / 1.83 h / 20 °C
2.1: acetyl bromide / CH2Cl2 / 2.5 h / 20 °C
3.1: 85 percent / sodium azide / dimethylsulfoxide / 11 h / 20 °C
4.1: H2; 20 percent Pd(OH)2/C; HCl / methanol; dioxane / 8 h / 20 °C
4.2: 89 percent / p-TsOH*H2O / toluene / 2.75 h / Heating
5.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexane / 0.75 h / -78.8 °C
5.2: dimethylaluminum chloride / tetrahydrofuran; hexane / 1 h / -78.8 °C
5.3: tetrahydrofuran; hexane / -85 - -20 °C
6.1: H2; 20 percent Pd(OH)2/C / methanol; acetic acid / 75 h / 20 °C / 2585.74 Torr
7.1: 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
1.1: 85 percent / sodium azide / dimethylsulfoxide / 11 h / 20 °C
2.1: H2; 20 percent Pd(OH)2/C; HCl / methanol; dioxane / 8 h / 20 °C
2.2: 89 percent / p-TsOH*H2O / toluene / 2.75 h / Heating
3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexane / 0.75 h / -78.8 °C
3.2: dimethylaluminum chloride / tetrahydrofuran; hexane / 1 h / -78.8 °C
3.3: tetrahydrofuran; hexane / -85 - -20 °C
4.1: H2; 20 percent Pd(OH)2/C / methanol; acetic acid / 75 h / 20 °C / 2585.74 Torr
5.1: 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
1.1: H2; 20 percent Pd(OH)2/C; HCl / methanol; dioxane / 8 h / 20 °C
1.2: 89 percent / p-TsOH*H2O / toluene / 2.75 h / Heating
2.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexane / 0.75 h / -78.8 °C
2.2: dimethylaluminum chloride / tetrahydrofuran; hexane / 1 h / -78.8 °C
2.3: tetrahydrofuran; hexane / -85 - -20 °C
3.1: H2; 20 percent Pd(OH)2/C / methanol; acetic acid / 75 h / 20 °C / 2585.74 Torr
4.1: 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: H2; 20 percent Pd(OH)2/C / methanol; acetic acid / 75 h / 20 °C / 2585.74 Torr
2: 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: O3; Me2S
2: NaClO2; NaH2PO4
3: HCOONH4 / Pd black
4: 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: 78 percent / PPTS / benzene / Heating
2: 100 percent / H2 / Lindlar catalyst / methanol / 20 °C
3: MnO2; 4 Angstroem molecular sieves / CH2Cl2 / Heating
4: NaCNBH3; AcOH / methanol / 0 °C
5: 83 percent / KHMDS / tetrahydrofuran; toluene / 6 h / -30 °C
6: 93 percent / TPAP; 4-Angstroem molecular sieves; NMO / acetonitrile
7: aq. NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0 °C
8: NaBH4 / methanol / 20 °C
9: 96 percent / K2OsO2(OH)4; aq. citric acid; NMO / 2-methyl-propan-2-ol / 20 °C
10: 100 percent / tetrahydrofuran / Heating
11: n-Bu3SnH; AIBN / toluene / Heating
12: 90 percent / dimethyldioxirane / acetone / 18 h / 0 - 3 °C
13: 35 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C
14: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C
15: 74 percent / NaOMe / methanol / 20 °C
View Scheme
参考文献
Hayes, Christopher J.; Sherlock, Alexandra E.; Selby, Matthew D.
Organic and Biomolecular Chemistry, 2006 , vol. 4, # 2 p. 193 - 195
反应条件
1: 100 percent / H2 / Lindlar catalyst / methanol / 20 °C
2: MnO2; 4 Angstroem molecular sieves / CH2Cl2 / Heating
3: NaCNBH3; AcOH / methanol / 0 °C
4: 83 percent / KHMDS / tetrahydrofuran; toluene / 6 h / -30 °C
5: 93 percent / TPAP; 4-Angstroem molecular sieves; NMO / acetonitrile
6: aq. NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0 °C
7: NaBH4 / methanol / 20 °C
8: 96 percent / K2OsO2(OH)4; aq. citric acid; NMO / 2-methyl-propan-2-ol / 20 °C
9: 100 percent / tetrahydrofuran / Heating
10: n-Bu3SnH; AIBN / toluene / Heating
11: 90 percent / dimethyldioxirane / acetone / 18 h / 0 - 3 °C
12: 35 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C
13: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C
14: 74 percent / NaOMe / methanol / 20 °C
View Scheme
参考文献
Hayes, Christopher J.; Sherlock, Alexandra E.; Selby, Matthew D.
Organic and Biomolecular Chemistry, 2006 , vol. 4, # 2 p. 193 - 195
反应条件
1: 77 percent / NaN3; B(OMe)3 / dimethylformamide / 50 °C
2: 78 percent / PPTS / benzene / Heating
3: 100 percent / H2 / Lindlar catalyst / methanol / 20 °C
4: MnO2; 4 Angstroem molecular sieves / CH2Cl2 / Heating
5: NaCNBH3; AcOH / methanol / 0 °C
6: 83 percent / KHMDS / tetrahydrofuran; toluene / 6 h / -30 °C
7: 93 percent / TPAP; 4-Angstroem molecular sieves; NMO / acetonitrile
8: aq. NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0 °C
9: NaBH4 / methanol / 20 °C
10: 96 percent / K2OsO2(OH)4; aq. citric acid; NMO / 2-methyl-propan-2-ol / 20 °C
11: 100 percent / tetrahydrofuran / Heating
12: n-Bu3SnH; AIBN / toluene / Heating
13: 90 percent / dimethyldioxirane / acetone / 18 h / 0 - 3 °C
14: 35 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C
15: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C
16: 74 percent / NaOMe / methanol / 20 °C
View Scheme
参考文献
Hayes, Christopher J.; Sherlock, Alexandra E.; Selby, Matthew D.
Organic and Biomolecular Chemistry, 2006 , vol. 4, # 2 p. 193 - 195
反应条件
1: NaHCO3; O3 / CH2Cl2; methanol / 1 h / -78 °C
2: 46 percent / PCC; Celite / CH2Cl2
3: 80 percent / p-TsOH*H2O / acetone / 25 h / 20 °C
4: PDC; Celite / dimethylformamide / 52 h / 20 °C
5: 1.11 g / tetrahydrofuran; diethyl ether / 0 °C
6: 97 percent Turnov. / diethyl ether / 20 h / 20 °C
7: 100 percent / p-TsOH*H2O / methanol / 24 h / 60 °C
8: pyridine / 3 h / 20 °C
9: 165 mg / pyridine; 4-(dimethylamino)pyridine / 27 h / 20 °C
10: 99 percent / HF / acetonitrile / 7 h / 20 °C
11: H2CrO4 / acetone / 6 h / 0 - 20 °C
12: aq. NaOH / 10 h / 20 °C
View Scheme
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
1: 46 percent / PCC; Celite / CH2Cl2
2: 80 percent / p-TsOH*H2O / acetone / 25 h / 20 °C
3: PDC; Celite / dimethylformamide / 52 h / 20 °C
4: 1.11 g / tetrahydrofuran; diethyl ether / 0 °C
5: 97 percent Turnov. / diethyl ether / 20 h / 20 °C
6: 100 percent / p-TsOH*H2O / methanol / 24 h / 60 °C
7: pyridine / 3 h / 20 °C
8: 165 mg / pyridine; 4-(dimethylamino)pyridine / 27 h / 20 °C
9: 99 percent / HF / acetonitrile / 7 h / 20 °C
10: H2CrO4 / acetone / 6 h / 0 - 20 °C
11: aq. NaOH / 10 h / 20 °C
View Scheme
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
