(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: 160 mg / toluene / 89 h / 140 °C
2.1: 72 percent / trifluoroacetic acid / H2O / 5 h / 0 °C
3.1: sodium periodate / methanol; H2O / 28 h / 0 - 20 °C
4.1: Jones reagent / acetone / 22 h / 0 - 5 °C
5.1: 1.34 g / NaBH4 / methanol / 3 h / 0 - 20 °C
6.1: 92 percent / 2,6-lutidine / CH2Cl2 / 43 h / 0 - 20 °C
7.1: 75 percent / sodium / liquid ammonia; tetrahydrofuran / 0.5 h / -78 °C
8.1: pyridine; trifluoroacetic acid; N,N'-dicyclohexylcarbodiimide / dimethylsulfoxide; benzene / 5 h / 20 °C
9.1: 41 mg / tetrahydrofuran / 13.75 h / -15 - 20 °C
10.1: 78 percent / pyridine; trifluoroacetic acid; N,N'-dicyclohexylcarbodiimide / dimethylsulfoxide; benzene / 7 h / 20 °C
11.1: 70 percent / triisobutylaluminum / hexane; 1,2-dichloro-ethane / 3.8 h / 0 - 20 °C
12.1: aq. trifluoroacetic acid / 17 h / 20 - 50 °C
12.2: 76 percent / sodium methoxide / methanol / 3 h / 0 °C
13.1: ozone / methanol / 0.08 h / -78 °C
13.2: dimethyl sulfide / methanol / 5 h / -78 - 20 °C
14.1: 27 mg / HOSO2NH2; NaH2PO4*2H2O; NaClO2 / 2-methyl-propan-2-ol; H2O / 0.25 h
View Scheme
参考文献
Chida, Noritaka; Takeoka, Jun; Ando, Kohji; Tsutsumi, Noriko; Ogawa, Seiichiro
Tetrahedron, 1997 , vol. 53, # 48 p. 16287 - 16298
反应条件
1.1: 72 percent / trifluoroacetic acid / H2O / 5 h / 0 °C
2.1: sodium periodate / methanol; H2O / 28 h / 0 - 20 °C
3.1: Jones reagent / acetone / 22 h / 0 - 5 °C
4.1: 1.34 g / NaBH4 / methanol / 3 h / 0 - 20 °C
5.1: 92 percent / 2,6-lutidine / CH2Cl2 / 43 h / 0 - 20 °C
6.1: 75 percent / sodium / liquid ammonia; tetrahydrofuran / 0.5 h / -78 °C
7.1: pyridine; trifluoroacetic acid; N,N'-dicyclohexylcarbodiimide / dimethylsulfoxide; benzene / 5 h / 20 °C
8.1: 41 mg / tetrahydrofuran / 13.75 h / -15 - 20 °C
9.1: 78 percent / pyridine; trifluoroacetic acid; N,N'-dicyclohexylcarbodiimide / dimethylsulfoxide; benzene / 7 h / 20 °C
10.1: 70 percent / triisobutylaluminum / hexane; 1,2-dichloro-ethane / 3.8 h / 0 - 20 °C
11.1: aq. trifluoroacetic acid / 17 h / 20 - 50 °C
11.2: 76 percent / sodium methoxide / methanol / 3 h / 0 °C
12.1: ozone / methanol / 0.08 h / -78 °C
12.2: dimethyl sulfide / methanol / 5 h / -78 - 20 °C
13.1: 27 mg / HOSO2NH2; NaH2PO4*2H2O; NaClO2 / 2-methyl-propan-2-ol; H2O / 0.25 h
View Scheme
参考文献
Chida, Noritaka; Takeoka, Jun; Ando, Kohji; Tsutsumi, Noriko; Ogawa, Seiichiro
Tetrahedron, 1997 , vol. 53, # 48 p. 16287 - 16298
反应条件
1: 80 percent / p-TsOH*H2O / acetone / 25 h / 20 °C
2: PDC; Celite / dimethylformamide / 52 h / 20 °C
3: 1.11 g / tetrahydrofuran; diethyl ether / 0 °C
4: 97 percent Turnov. / diethyl ether / 20 h / 20 °C
5: 100 percent / p-TsOH*H2O / methanol / 24 h / 60 °C
6: pyridine / 3 h / 20 °C
7: 165 mg / pyridine; 4-(dimethylamino)pyridine / 27 h / 20 °C
8: 99 percent / HF / acetonitrile / 7 h / 20 °C
9: H2CrO4 / acetone / 6 h / 0 - 20 °C
10: 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
1.1: 40 percent / isopropylmagnesium bromide / tetrahydrofuran / 11 h / 4 °C
2.1: 4-(dimethylamino)pyridine; pyridine / 2 h / 20 °C
3.1: 3.1 g / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 11 h / 20 °C
4.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C
5.1: 1.93 g / NaHCO3; H2O2 / tetrahydrofuran; ethyl acetate / 0.5 h / 20 °C
6.1: (diethylamino)diphenylsilyllithium; diethyl zinc / tetrahydrofuran; hexane / -78 °C
6.2: 57 percent / m-chloroperoxybenzoic acid; KHF2 / dimethylformamide / 2 h / 20 °C
7.1: 58 percent / BuLi; HMPA; diisopropylamine / hexane; tetrahydrofuran / 4 h / -78 °C
8.1: 355 mg / trifluoroacetic acid / CH2Cl2 / 3 h / 20 °C
9.1: NaOH / H2O / 64 h / 4 °C
View Scheme
参考文献
Fukuda, Nobuhisa; Sasaki, Kazuki; Sastry; Kanai, Motomu; Shibasaki, Masakatsu
Journal of Organic Chemistry, 2006 , vol. 71, # 3 p. 1220 - 1225
反应条件
1.1: 4-(dimethylamino)pyridine; pyridine / 2 h / 20 °C
2.1: 3.1 g / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 11 h / 20 °C
3.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C
4.1: 1.93 g / NaHCO3; H2O2 / tetrahydrofuran; ethyl acetate / 0.5 h / 20 °C
5.1: (diethylamino)diphenylsilyllithium; diethyl zinc / tetrahydrofuran; hexane / -78 °C
5.2: 57 percent / m-chloroperoxybenzoic acid; KHF2 / dimethylformamide / 2 h / 20 °C
6.1: 58 percent / BuLi; HMPA; diisopropylamine / hexane; tetrahydrofuran / 4 h / -78 °C
7.1: 355 mg / trifluoroacetic acid / CH2Cl2 / 3 h / 20 °C
8.1: NaOH / H2O / 64 h / 4 °C
View Scheme
参考文献
Fukuda, Nobuhisa; Sasaki, Kazuki; Sastry; Kanai, Motomu; Shibasaki, Masakatsu
Journal of Organic Chemistry, 2006 , vol. 71, # 3 p. 1220 - 1225
反应条件
1.1: ozone / methanol / 0.5 h / -78 °C
1.2: Me2S / methanol / 5 h / -78 - 20 °C
2.1: NaH2PO4; 2-methyl-2-butene; sodium chlorite / 2-methyl-propan-2-ol / 2 h / 20 °C
3.1: 134 mg / H2SO4 / ethanol / 9 h / 80 °C
4.1: 40 percent / isopropylmagnesium bromide / tetrahydrofuran / 11 h / 4 °C
5.1: 4-(dimethylamino)pyridine; pyridine / 2 h / 20 °C
6.1: 3.1 g / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 11 h / 20 °C
7.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C
8.1: 1.93 g / NaHCO3; H2O2 / tetrahydrofuran; ethyl acetate / 0.5 h / 20 °C
9.1: (diethylamino)diphenylsilyllithium; diethyl zinc / tetrahydrofuran; hexane / -78 °C
9.2: 57 percent / m-chloroperoxybenzoic acid; KHF2 / dimethylformamide / 2 h / 20 °C
10.1: 58 percent / BuLi; HMPA; diisopropylamine / hexane; tetrahydrofuran / 4 h / -78 °C
11.1: 355 mg / trifluoroacetic acid / CH2Cl2 / 3 h / 20 °C
12.1: NaOH / H2O / 64 h / 4 °C
View Scheme
参考文献
Fukuda, Nobuhisa; Sasaki, Kazuki; Sastry; Kanai, Motomu; Shibasaki, Masakatsu
Journal of Organic Chemistry, 2006 , vol. 71, # 3 p. 1220 - 1225
反应条件
1.1: (diethylamino)diphenylsilyllithium; diethyl zinc / tetrahydrofuran; hexane / -78 °C
1.2: 57 percent / m-chloroperoxybenzoic acid; KHF2 / dimethylformamide / 2 h / 20 °C
2.1: 58 percent / BuLi; HMPA; diisopropylamine / hexane; tetrahydrofuran / 4 h / -78 °C
3.1: 355 mg / trifluoroacetic acid / CH2Cl2 / 3 h / 20 °C
4.1: NaOH / H2O / 64 h / 4 °C
View Scheme
参考文献
Fukuda, Nobuhisa; Sasaki, Kazuki; Sastry; Kanai, Motomu; Shibasaki, Masakatsu
Journal of Organic Chemistry, 2006 , vol. 71, # 3 p. 1220 - 1225
反应条件
1.1: HCl / H2O / 5 h / 100 °C
2.1: thionyl chloride / 17 h / 80 °C
3.1: 68 percent / NaHCO3 / acetonitrile / 4 h / 70 °C
4.1: ozone / methanol / 0.5 h / -78 °C
4.2: Me2S / methanol / 5 h / -78 - 20 °C
5.1: NaH2PO4; 2-methyl-2-butene; sodium chlorite / 2-methyl-propan-2-ol / 2 h / 20 °C
6.1: 134 mg / H2SO4 / ethanol / 9 h / 80 °C
7.1: 40 percent / isopropylmagnesium bromide / tetrahydrofuran / 11 h / 4 °C
8.1: 4-(dimethylamino)pyridine; pyridine / 2 h / 20 °C
9.1: 3.1 g / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 11 h / 20 °C
10.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C
11.1: 1.93 g / NaHCO3; H2O2 / tetrahydrofuran; ethyl acetate / 0.5 h / 20 °C
12.1: (diethylamino)diphenylsilyllithium; diethyl zinc / tetrahydrofuran; hexane / -78 °C
12.2: 57 percent / m-chloroperoxybenzoic acid; KHF2 / dimethylformamide / 2 h / 20 °C
13.1: 58 percent / BuLi; HMPA; diisopropylamine / hexane; tetrahydrofuran / 4 h / -78 °C
14.1: 355 mg / trifluoroacetic acid / CH2Cl2 / 3 h / 20 °C
15.1: NaOH / H2O / 64 h / 4 °C
View Scheme
参考文献
Fukuda, Nobuhisa; Sasaki, Kazuki; Sastry; Kanai, Motomu; Shibasaki, Masakatsu
Journal of Organic Chemistry, 2006 , vol. 71, # 3 p. 1220 - 1225
反应条件
1.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C
2.1: 1.93 g / NaHCO3; H2O2 / tetrahydrofuran; ethyl acetate / 0.5 h / 20 °C
3.1: (diethylamino)diphenylsilyllithium; diethyl zinc / tetrahydrofuran; hexane / -78 °C
3.2: 57 percent / m-chloroperoxybenzoic acid; KHF2 / dimethylformamide / 2 h / 20 °C
4.1: 58 percent / BuLi; HMPA; diisopropylamine / hexane; tetrahydrofuran / 4 h / -78 °C
5.1: 355 mg / trifluoroacetic acid / CH2Cl2 / 3 h / 20 °C
6.1: NaOH / H2O / 64 h / 4 °C
View Scheme
参考文献
Fukuda, Nobuhisa; Sasaki, Kazuki; Sastry; Kanai, Motomu; Shibasaki, Masakatsu
Journal of Organic Chemistry, 2006 , vol. 71, # 3 p. 1220 - 1225
反应条件
1: 58 percent / BuLi; HMPA; diisopropylamine / hexane; tetrahydrofuran / 4 h / -78 °C
2: 355 mg / trifluoroacetic acid / CH2Cl2 / 3 h / 20 °C
3: NaOH / H2O / 64 h / 4 °C
View Scheme
参考文献
Fukuda, Nobuhisa; Sasaki, Kazuki; Sastry; Kanai, Motomu; Shibasaki, Masakatsu
Journal of Organic Chemistry, 2006 , vol. 71, # 3 p. 1220 - 1225
