[(3S,6S)-1-甲基-7-氧代-6-[[(E,2R,3R,4S,5R)-3,4,5-三羟基-2-甲氧基-8-甲基壬-6-烯酰基]氨基]氮杂环庚-3-基]十四烷酸酯合成路线 （共 31 条）
反应条件
1: 97 percent / LiOH / methanol; H2O / 1 h / 25 °C
2: 94.2 percent / EDCI; DMAP / CH2Cl2 / 16 h / 25 °C
3: 99 percent / TFA / CH2Cl2 / 2 h / 25 °C
4: 83 percent / propan-2-ol / 16 h / 80 °C
5: 73 percent / TFA / tetrahydrofuran; H2O / 0.33 h / 0 °C
View Scheme
参考文献
Kinder, Jr.; Wattanasin; Versace; Bair; Bontempo; Green; Lu; Marepalli; Phillips; Roche; Tran; Wang; Waykole; Xu; Zabludoff
Journal of Organic Chemistry, 2001 , vol. 66, # 6 p. 2118 - 2122
反应条件
1: 99 percent / TFA / CH2Cl2 / 2 h / 25 °C
2: 83 percent / propan-2-ol / 16 h / 80 °C
3: 73 percent / TFA / tetrahydrofuran; H2O / 0.33 h / 0 °C
View Scheme
参考文献
Kinder, Jr.; Wattanasin; Versace; Bair; Bontempo; Green; Lu; Marepalli; Phillips; Roche; Tran; Wang; Waykole; Xu; Zabludoff
Journal of Organic Chemistry, 2001 , vol. 66, # 6 p. 2118 - 2122
反应条件
1: NaOMe / methanol / 2 h / 20 °C
2: pyridine / 4 h / 0 °C
3: i-Pr2NEt / CH2Cl2 / 1 h / 0 °C
4: MeLi / CH2Cl2 / 4 h / -78 °C
5: 1) (COCl)2, DMSO 2) Et3N / 1) CH2Cl2, -78 to -40 deg C
6: NaClO2, NaH2PO4, 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.5 h / 0 to 20 deg C
7: 66 percent / HOBT, 1-(3-dimethylaminopropyl)-ethylcarbodiimide*HCl / CH2Cl2; dimethylformamide / 10 h / 0 to 20 deg C
8: 54 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C
View Scheme
参考文献
Broka; Ehrler
Tetrahedron Letters, 1991 , vol. 32, # 42 p. 5907 - 5910
反应条件
1: 1) (COCl)2, DMSO 2) Et3N / 1) CH2Cl2, -78 to -40 deg C
2: NaClO2, NaH2PO4, 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.5 h / 0 to 20 deg C
3: 66 percent / HOBT, 1-(3-dimethylaminopropyl)-ethylcarbodiimide*HCl / CH2Cl2; dimethylformamide / 10 h / 0 to 20 deg C
4: 54 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C
View Scheme
参考文献
Broka; Ehrler
Tetrahedron Letters, 1991 , vol. 32, # 42 p. 5907 - 5910
反应条件
1: 66 percent / HOBT, 1-(3-dimethylaminopropyl)-ethylcarbodiimide*HCl / CH2Cl2; dimethylformamide / 10 h / 0 to 20 deg C
2: 54 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C
View Scheme
参考文献
Broka; Ehrler
Tetrahedron Letters, 1991 , vol. 32, # 42 p. 5907 - 5910
反应条件
1: Na, NH3(l) / 0.08 h
2: pyridine / 4 h / 0 °C
3: i-Pr2NEt / CH2Cl2 / 1 h / 0 °C
4: MeLi / CH2Cl2 / 4 h / -78 °C
5: 1) (COCl)2, DMSO 2) Et3N / 1) CH2Cl2, -78 to -40 deg C
6: NaClO2, NaH2PO4, 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.5 h / 0 to 20 deg C
7: 66 percent / HOBT, 1-(3-dimethylaminopropyl)-ethylcarbodiimide*HCl / CH2Cl2; dimethylformamide / 10 h / 0 to 20 deg C
8: 54 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C
View Scheme
参考文献
Broka; Ehrler
Tetrahedron Letters, 1991 , vol. 32, # 42 p. 5907 - 5910
反应条件
1: Na(Hg), Na2HPO4 / methanol / 2 h / 20 °C
2: KH / tetrahydrofuran / 1.5 h / 20 °C
3: Na, NH3(l) / 0.08 h
4: pyridine / 4 h / 0 °C
5: i-Pr2NEt / CH2Cl2 / 1 h / 0 °C
6: MeLi / CH2Cl2 / 4 h / -78 °C
7: 1) (COCl)2, DMSO 2) Et3N / 1) CH2Cl2, -78 to -40 deg C
8: NaClO2, NaH2PO4, 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.5 h / 0 to 20 deg C
9: 66 percent / HOBT, 1-(3-dimethylaminopropyl)-ethylcarbodiimide*HCl / CH2Cl2; dimethylformamide / 10 h / 0 to 20 deg C
10: 54 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C
View Scheme
参考文献
Broka; Ehrler
Tetrahedron Letters, 1991 , vol. 32, # 42 p. 5907 - 5910
反应条件
1: 1) n-BuLi / 1) THF, -78 deg C, 15 min, 2) -78 to 20 deg C, 90 min
2: Na(Hg), Na2HPO4 / methanol / 2 h / 20 °C
3: KH / tetrahydrofuran / 1.5 h / 20 °C
4: Na, NH3(l) / 0.08 h
5: pyridine / 4 h / 0 °C
6: i-Pr2NEt / CH2Cl2 / 1 h / 0 °C
7: MeLi / CH2Cl2 / 4 h / -78 °C
8: 1) (COCl)2, DMSO 2) Et3N / 1) CH2Cl2, -78 to -40 deg C
9: NaClO2, NaH2PO4, 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.5 h / 0 to 20 deg C
10: 66 percent / HOBT, 1-(3-dimethylaminopropyl)-ethylcarbodiimide*HCl / CH2Cl2; dimethylformamide / 10 h / 0 to 20 deg C
11: 54 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C
View Scheme
参考文献
Broka; Ehrler
Tetrahedron Letters, 1991 , vol. 32, # 42 p. 5907 - 5910
反应条件
1.1: 69 percent / dioxane / 30 h / Heating
2.1: DDQ / CH2Cl2; methanol / 2 h / 20 °C
2.2: 89 percent / PPTS / CH2Cl2; methanol / 6 h / 45 °C
View Scheme
参考文献
Boeckman Jr., Robert K.; Clark, Tammy J.; Shook, Brian C.
Helvetica Chimica Acta, 2002 , vol. 85, # 12 p. 4532 - 4560
反应条件
1: 33 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP / CH2Cl2; tetrahydrofuran / -50 - -15 °C
2: 50 percent / TFA / tetrahydrofuran; H2O / -15 - 20 °C
View Scheme
参考文献
Chida, Noritaka; Tobe, Takahiko; Murai, Katsuyuki; Yamazaki, Kaori; Ogawa, Seiichiro
Heterocycles, 1994 , vol. 38, # 11 p. 2383 - 2388
