[(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: With 2,3-dicyano-5,6-dichloro-p-benzoquinone in methanol; dichloromethane
T=20°C; 2 h;
2: With pyridinium p-toluenesulfonate in methanol; dichloromethane
T=45°C; 6 h;
参考文献
Boeckman Jr., Robert K.; Clark, Tammy J.; Shook, Brian C.
Organic Letters, 2002 , vol. 4, # 12 p. 2109 - 2112
反应条件
trifluoroacetic acid in tetrahydrofuran; water
T=0°C; 0.333333 h;
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
tetrabutyl ammonium fluoride in tetrahydrofuran
T=20°C; 1.5 h;
参考文献
Broka; Ehrler
Tetrahedron Letters, 1991 , vol. 32, # 42 p. 5907 - 5910
反应条件
1.1: 0.39 g / H2 / Pearlman's catalyst / ethanol / 11 h
2.1: 88 percent / NaOMe / methanol / 1.5 h / 85 °C
3.1: 90 percent / TFA / 20 °C
4.1: 69 percent / dioxane / 30 h / Heating
5.1: DDQ / CH2Cl2; methanol / 2 h / 20 °C
5.2: 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
1.1: 98 percent / methanol / 13 h / 20 °C
2.1: 86 percent / citric acid; water / tetrahydrofuran / 0.5 h / 20 °C
3.1: 0.39 g / H2 / Pearlman's catalyst / ethanol / 11 h
4.1: 88 percent / NaOMe / methanol / 1.5 h / 85 °C
5.1: 90 percent / TFA / 20 °C
6.1: 69 percent / dioxane / 30 h / Heating
7.1: DDQ / CH2Cl2; methanol / 2 h / 20 °C
7.2: 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
1.1: 86 percent / citric acid; water / tetrahydrofuran / 0.5 h / 20 °C
2.1: 0.39 g / H2 / Pearlman's catalyst / ethanol / 11 h
3.1: 88 percent / NaOMe / methanol / 1.5 h / 85 °C
4.1: 90 percent / TFA / 20 °C
5.1: 69 percent / dioxane / 30 h / Heating
6.1: DDQ / CH2Cl2; methanol / 2 h / 20 °C
6.2: 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
1.1: iPrNEt; Et2BOTf / CH2Cl2 / -78 °C / 1 Torr
1.2: tetrahydrofuran / 23 h / -40 °C
1.3: 70 percent / 1H-imidazole / CH2Cl2 / 11 h / 20 °C
2.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.2: 91 percent / tetrahydrofuran / 10 h / -40 °C
3.1: 99 percent / DIBAL / toluene / 0.75 h / -78 °C
4.1: SnCl4 / heptane; CH2Cl2 / 0.75 h / -78 °C
4.2: 62 percent / heptane; CH2Cl2 / 1.5 h / -78 °C
5.1: 69 percent / dioxane / 30 h / Heating
6.1: DDQ / CH2Cl2; methanol / 2 h / 20 °C
6.2: 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: 1) NaN(SiMe3)2 / 1) THF, 20 deg C, 15 min 2) THF, 20 deg C, 90 min
2: H2 / Pd/C / ethanol / 24 h / 20 °C / 2585.7 Torr
4: LiOH, H2O2 / tetrahydrofuran; H2O / 0.5 h / 0 °C
5: TFA / CH2Cl2 / 30 h / 20 °C
6: HOBT, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide*HCl / CH2Cl2 / 3 h / 0 to 20 deg c
7: H2 / Pd/C / ethyl acetate / 2 h / 20 °C
8: Et3N / tetrahydrofuran / 3 h / 0 °C
9: TBAF / tetrahydrofuran / 3 h / 0 °C
10: Et3N, DMAP / CH2Cl2 / 3 h / 20 °C
11: H2 / Pd/C / methanol; ethyl acetate
12: 66 percent / HOBT, 1-(3-dimethylaminopropyl)-ethylcarbodiimide*HCl / CH2Cl2; dimethylformamide / 10 h / 0 to 20 deg C
13: 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: H2 / Pd/C / ethyl acetate / 2 h / 20 °C
2: Et3N / tetrahydrofuran / 3 h / 0 °C
3: TBAF / tetrahydrofuran / 3 h / 0 °C
4: Et3N, DMAP / CH2Cl2 / 3 h / 20 °C
5: H2 / Pd/C / methanol; ethyl acetate
6: 66 percent / HOBT, 1-(3-dimethylaminopropyl)-ethylcarbodiimide*HCl / CH2Cl2; dimethylformamide / 10 h / 0 to 20 deg C
7: 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: H2 / Pd/C / ethanol / 24 h / 20 °C / 2585.7 Torr
3: LiOH, H2O2 / tetrahydrofuran; H2O / 0.5 h / 0 °C
4: TFA / CH2Cl2 / 30 h / 20 °C
5: HOBT, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide*HCl / CH2Cl2 / 3 h / 0 to 20 deg c
6: H2 / Pd/C / ethyl acetate / 2 h / 20 °C
7: Et3N / tetrahydrofuran / 3 h / 0 °C
8: TBAF / tetrahydrofuran / 3 h / 0 °C
9: Et3N, DMAP / CH2Cl2 / 3 h / 20 °C
10: H2 / Pd/C / methanol; ethyl acetate
11: 66 percent / HOBT, 1-(3-dimethylaminopropyl)-ethylcarbodiimide*HCl / CH2Cl2; dimethylformamide / 10 h / 0 to 20 deg C
12: 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
