[(1S,3S)-3-[[4-甲氧基-3-(3-甲氧基丙氧基)苯基]甲基]-4-甲基-1-[(2S,4S)-四氢-4-异丙基-5-氧代-2-呋喃基]戊基]-氨基甲酸叔丁酯合成路线 （共 84 条）
反应条件
1.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
1.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
2.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
2.2: 39 mg / H2 / Pd/C / ethanol / 48 h
3.1: 63 percent / Et3N / tetrahydrofuran / 18 h / 20 °C
View Scheme
参考文献
Lindsay, Karl B.; Skrydstrup, Troels
Journal of Organic Chemistry, 2006 , vol. 71, # 13 p. 4766 - 4777
反应条件
1.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
2.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
2.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
3.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
3.2: 39 mg / H2 / Pd/C / ethanol / 48 h
4.1: 63 percent / Et3N / tetrahydrofuran / 18 h / 20 °C
View Scheme
参考文献
Lindsay, Karl B.; Skrydstrup, Troels
Journal of Organic Chemistry, 2006 , vol. 71, # 13 p. 4766 - 4777
反应条件
1.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
2.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
3.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
3.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
4.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
4.2: 39 mg / H2 / Pd/C / ethanol / 48 h
5.1: 63 percent / Et3N / tetrahydrofuran / 18 h / 20 °C
View Scheme
参考文献
Lindsay, Karl B.; Skrydstrup, Troels
Journal of Organic Chemistry, 2006 , vol. 71, # 13 p. 4766 - 4777
反应条件
1.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
2.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
3.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
4.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
5.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
6.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
6.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
7.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
7.2: 39 mg / H2 / Pd/C / ethanol / 48 h
8.1: 63 percent / Et3N / tetrahydrofuran / 18 h / 20 °C
View Scheme
参考文献
Lindsay, Karl B.; Skrydstrup, Troels
Journal of Organic Chemistry, 2006 , vol. 71, # 13 p. 4766 - 4777
反应条件
1: 94 percent / H2 / Pd/C / ethanol / 18 h
2: 63 percent / Et3N / tetrahydrofuran / 18 h / 20 °C
View Scheme
参考文献
Lindsay, Karl B.; Skrydstrup, Troels
Journal of Organic Chemistry, 2006 , vol. 71, # 13 p. 4766 - 4777
反应条件
1: NaBH4 / ethanol
2: PBr3 / CH2Cl2
3: 76 percent / LiHMDS / tetrahydrofuran
4: 81 percent / LiOH; H2O2
5: 95 percent / LAH / tetrahydrofuran
6: 97 percent / PPh3; NBS / CH2Cl2
7: 68 percent / n-BuLi
8: HCl / acetonitrile
9: Et3N
10: NaBH4 / ethanol
11: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
12: Mg
13: 23 percent / H2 / Pd(OH)2/C
14: 38 percent / TPAP; NMMO
View Scheme
参考文献
Dong, Hua; Zhang, Zhi-Liu; Huang, Jia-Hui; Ma, Rujian; Chen, Shu-Hui; Li, Ge
Tetrahedron Letters, 2005 , vol. 46, # 37 p. 6337 - 6340
反应条件
1: 97 percent / PPh3; NBS / CH2Cl2
2: 68 percent / n-BuLi
3: HCl / acetonitrile
4: Et3N
5: NaBH4 / ethanol
6: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
7: Mg
8: 23 percent / H2 / Pd(OH)2/C
9: 38 percent / TPAP; NMMO
View Scheme
参考文献
Dong, Hua; Zhang, Zhi-Liu; Huang, Jia-Hui; Ma, Rujian; Chen, Shu-Hui; Li, Ge
Tetrahedron Letters, 2005 , vol. 46, # 37 p. 6337 - 6340
反应条件
1: 95 percent / LAH / tetrahydrofuran
2: 97 percent / PPh3; NBS / CH2Cl2
3: 68 percent / n-BuLi
4: HCl / acetonitrile
5: Et3N
6: NaBH4 / ethanol
7: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
8: Mg
9: 23 percent / H2 / Pd(OH)2/C
10: 38 percent / TPAP; NMMO
View Scheme
参考文献
Dong, Hua; Zhang, Zhi-Liu; Huang, Jia-Hui; Ma, Rujian; Chen, Shu-Hui; Li, Ge
Tetrahedron Letters, 2005 , vol. 46, # 37 p. 6337 - 6340
反应条件
1.1: thionyl chloride / dichloromethane / 3 h / 20 °C / Inert atmosphere
2.1: n-butyllithium; n-butyl-magnesium bromide / hexane; tetrahydrofuran / 0 °C
2.2: 5 h / -78 °C / Inert atmosphere
3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine; hydrogen / palladium 10 on activated carbon / tetrahydrofuran / 24 h / 20 °C
View Scheme
参考文献
CarboDesign LLC
Patent: US2011/137047 A1, 2011 ;
反应条件
1: 76 percent / LiHMDS / tetrahydrofuran
2: 81 percent / LiOH; H2O2
3: 95 percent / LAH / tetrahydrofuran
4: 97 percent / PPh3; NBS / CH2Cl2
5: 68 percent / n-BuLi
6: HCl / acetonitrile
7: Et3N
8: NaBH4 / ethanol
9: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
10: Mg
11: 23 percent / H2 / Pd(OH)2/C
12: 38 percent / TPAP; NMMO
View Scheme
参考文献
Dong, Hua; Zhang, Zhi-Liu; Huang, Jia-Hui; Ma, Rujian; Chen, Shu-Hui; Li, Ge
Tetrahedron Letters, 2005 , vol. 46, # 37 p. 6337 - 6340
