[(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
1.1: 56 mg / imidazole / CH2Cl2 / 11 h / 20 °C
2.1: 91 percent / tetrahydrofuran; various solvent(s) / -78 - -40 °C
3.1: 99 percent / DIBAL-H / toluene; various solvent(s) / 0.75 h / -78 °C
4.1: 62 percent / SnCl4 / CH2Cl2; heptane / 1.5 h / -78 °C
5.1: 68 percent / dioxane / 30 h / Heating
6.1: DDQ / methanol; CH2Cl2 / 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.
Organic Letters, 2002 , vol. 4, # 12 p. 2109 - 2112
反应条件
1: 82 percent / Ag2O; H2O / CH2Cl2 / 18 h / 15 - 30 °C
2: 67.6 percent / acetic acid; H2O / 20 °C
3: 85 percent / NaIO4 / methanol; H2O / 0.67 h / 8 °C
4: 28.5 percent / CrCl2 / tetrahydrofuran; dimethylformamide / 1.5 h
5: 83 percent / propan-2-ol / 16 h / 80 °C
6: 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: 67.6 percent / acetic acid; H2O / 20 °C
2: 85 percent / NaIO4 / methanol; H2O / 0.67 h / 8 °C
3: 28.5 percent / CrCl2 / tetrahydrofuran; dimethylformamide / 1.5 h
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: 83 percent / propan-2-ol / 16 h / 80 °C
2: 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: 94.2 percent / EDCI; DMAP / CH2Cl2 / 16 h / 25 °C
2: 99 percent / TFA / CH2Cl2 / 2 h / 25 °C
3: 83 percent / propan-2-ol / 16 h / 80 °C
4: 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: 86.5 percent / I2
2: 82 percent / Ag2O; H2O / CH2Cl2 / 18 h / 15 - 30 °C
3: 67.6 percent / acetic acid; H2O / 20 °C
4: 85 percent / NaIO4 / methanol; H2O / 0.67 h / 8 °C
5: 28.5 percent / CrCl2 / tetrahydrofuran; dimethylformamide / 1.5 h
6: 83 percent / propan-2-ol / 16 h / 80 °C
7: 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: 28.5 percent / CrCl2 / tetrahydrofuran; dimethylformamide / 1.5 h
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: 85 percent / NaIO4 / methanol; H2O / 0.67 h / 8 °C
2: 28.5 percent / CrCl2 / tetrahydrofuran; dimethylformamide / 1.5 h
3: 83 percent / propan-2-ol / 16 h / 80 °C
4: 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: 78 percent / PPh3; DEAD / tetrahydrofuran / 14 h / 20 °C
2: 83 percent / KHMDS / tetrahydrofuran / 18 h / -78 - 25 °C
3: 97 percent / LiOH / methanol; H2O / 1 h / 25 °C
4: 94.2 percent / EDCI; DMAP / CH2Cl2 / 16 h / 25 °C
5: 99 percent / TFA / CH2Cl2 / 2 h / 25 °C
6: 83 percent / propan-2-ol / 16 h / 80 °C
7: 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: 83 percent / KHMDS / tetrahydrofuran / 18 h / -78 - 25 °C
2: 97 percent / LiOH / methanol; H2O / 1 h / 25 °C
3: 94.2 percent / EDCI; DMAP / CH2Cl2 / 16 h / 25 °C
4: 99 percent / TFA / CH2Cl2 / 2 h / 25 °C
5: 83 percent / propan-2-ol / 16 h / 80 °C
6: 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
