2-[[(3R,4S,7S,10S,11R)-3-乙基-11,15-二羟基-3-甲基-10-甲基氨基-6,9-二氧代-7-丙-2-基2-氧杂-5,8-二氮杂双环[10.3.1]十六碳-1(15),12(16),13-三烯-4-羰基]氨基]乙酸合成路线 （共 26 条）
反应条件
1: H2; 2,2'-bipyridyl / Pd/C / methanol; ethyl acetate / 2 h
2: 37.7 mg / 2,4,6-collidine / CH2Cl2 / 3 h / 20 °C
3: Dess-Martin periodinane / CH2Cl2 / 1.25 h / 0 - 25 °C
4: aq. NaClO2; NaH2PO4*2H2O / 2-methyl-propan-2-ol; various solvent(s) / 0.33 h / 25 °C
5: 28.4 mg / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; i-Pr2NEt2 / tetrahydrofuran / 18 h / 20 °C
6: 77 percent / MTBD / dimethylformamide / 1.5 h / 20 °C
7: 96 percent / n-Bu4NF; AcOH / tetrahydrofuran / 3 h / 20 °C
8: 74 percent / β-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C
9: 85 percent / H2; aq. HCl / Pd black / ethanol / 2 h
View Scheme
参考文献
Cao, Bin; Park, Haengsoon; Joullie, Madeleine M.
Journal of the American Chemical Society, 2002 , vol. 124, # 4 p. 520 - 521
反应条件
1: 88 percent / β-bromocatecholborane / CH2Cl2 / 0.5 h / -78 °C
2: H2; 2,2'-bipyridyl / Pd/C / methanol; ethyl acetate / 2 h
3: 37.7 mg / 2,4,6-collidine / CH2Cl2 / 3 h / 20 °C
4: Dess-Martin periodinane / CH2Cl2 / 1.25 h / 0 - 25 °C
5: aq. NaClO2; NaH2PO4*2H2O / 2-methyl-propan-2-ol; various solvent(s) / 0.33 h / 25 °C
6: 28.4 mg / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; i-Pr2NEt2 / tetrahydrofuran / 18 h / 20 °C
7: 77 percent / MTBD / dimethylformamide / 1.5 h / 20 °C
8: 96 percent / n-Bu4NF; AcOH / tetrahydrofuran / 3 h / 20 °C
9: 74 percent / β-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C
10: 85 percent / H2; aq. HCl / Pd black / ethanol / 2 h
View Scheme
参考文献
Cao, Bin; Park, Haengsoon; Joullie, Madeleine M.
Journal of the American Chemical Society, 2002 , vol. 124, # 4 p. 520 - 521
反应条件
1: Dess-Martin periodinane / CH2Cl2 / 1.25 h / 0 - 25 °C
2: aq. NaClO2; NaH2PO4*2H2O / 2-methyl-propan-2-ol; various solvent(s) / 0.33 h / 25 °C
3: 28.4 mg / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; i-Pr2NEt2 / tetrahydrofuran / 18 h / 20 °C
4: 77 percent / MTBD / dimethylformamide / 1.5 h / 20 °C
5: 96 percent / n-Bu4NF; AcOH / tetrahydrofuran / 3 h / 20 °C
6: 74 percent / β-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C
7: 85 percent / H2; aq. HCl / Pd black / ethanol / 2 h
View Scheme
参考文献
Cao, Bin; Park, Haengsoon; Joullie, Madeleine M.
Journal of the American Chemical Society, 2002 , vol. 124, # 4 p. 520 - 521
反应条件
1: 78 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole / dimethylformamide; CH2Cl2 / 24 h / 0 - 20 °C
2: 88 percent / β-bromocatecholborane / CH2Cl2 / 0.5 h / -78 °C
3: H2; 2,2'-bipyridyl / Pd/C / methanol; ethyl acetate / 2 h
4: 37.7 mg / 2,4,6-collidine / CH2Cl2 / 3 h / 20 °C
5: Dess-Martin periodinane / CH2Cl2 / 1.25 h / 0 - 25 °C
6: aq. NaClO2; NaH2PO4*2H2O / 2-methyl-propan-2-ol; various solvent(s) / 0.33 h / 25 °C
7: 28.4 mg / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; i-Pr2NEt2 / tetrahydrofuran / 18 h / 20 °C
8: 77 percent / MTBD / dimethylformamide / 1.5 h / 20 °C
9: 96 percent / n-Bu4NF; AcOH / tetrahydrofuran / 3 h / 20 °C
10: 74 percent / β-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C
11: 85 percent / H2; aq. HCl / Pd black / ethanol / 2 h
View Scheme
参考文献
Cao, Bin; Park, Haengsoon; Joullie, Madeleine M.
Journal of the American Chemical Society, 2002 , vol. 124, # 4 p. 520 - 521
反应条件
1: 2,6-lutidine / CH2Cl2 / 1 h / 20 °C
2: 143 mg / aq. LiOH / 2-methyl-propan-2-ol / 16 h / 20 °C
3: 78 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole / dimethylformamide; CH2Cl2 / 24 h / 0 - 20 °C
4: 88 percent / β-bromocatecholborane / CH2Cl2 / 0.5 h / -78 °C
5: H2; 2,2'-bipyridyl / Pd/C / methanol; ethyl acetate / 2 h
6: 37.7 mg / 2,4,6-collidine / CH2Cl2 / 3 h / 20 °C
7: Dess-Martin periodinane / CH2Cl2 / 1.25 h / 0 - 25 °C
8: aq. NaClO2; NaH2PO4*2H2O / 2-methyl-propan-2-ol; various solvent(s) / 0.33 h / 25 °C
9: 28.4 mg / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; i-Pr2NEt2 / tetrahydrofuran / 18 h / 20 °C
10: 77 percent / MTBD / dimethylformamide / 1.5 h / 20 °C
11: 96 percent / n-Bu4NF; AcOH / tetrahydrofuran / 3 h / 20 °C
12: 74 percent / β-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C
13: 85 percent / H2; aq. HCl / Pd black / ethanol / 2 h
View Scheme
参考文献
Cao, Bin; Park, Haengsoon; Joullie, Madeleine M.
Journal of the American Chemical Society, 2002 , vol. 124, # 4 p. 520 - 521
反应条件
1: 74 percent / β-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C
2: 85 percent / H2; aq. HCl / Pd black / ethanol / 2 h
View Scheme
参考文献
Cao, Bin; Park, Haengsoon; Joullie, Madeleine M.
Journal of the American Chemical Society, 2002 , vol. 124, # 4 p. 520 - 521
反应条件
1: 96 percent / n-Bu4NF; AcOH / tetrahydrofuran / 3 h / 20 °C
2: 74 percent / β-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C
3: 85 percent / H2; aq. HCl / Pd black / ethanol / 2 h
View Scheme
参考文献
Cao, Bin; Park, Haengsoon; Joullie, Madeleine M.
Journal of the American Chemical Society, 2002 , vol. 124, # 4 p. 520 - 521
反应条件
1: 143 mg / aq. LiOH / 2-methyl-propan-2-ol / 16 h / 20 °C
2: 78 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole / dimethylformamide; CH2Cl2 / 24 h / 0 - 20 °C
3: 88 percent / β-bromocatecholborane / CH2Cl2 / 0.5 h / -78 °C
4: H2; 2,2'-bipyridyl / Pd/C / methanol; ethyl acetate / 2 h
5: 37.7 mg / 2,4,6-collidine / CH2Cl2 / 3 h / 20 °C
6: Dess-Martin periodinane / CH2Cl2 / 1.25 h / 0 - 25 °C
7: aq. NaClO2; NaH2PO4*2H2O / 2-methyl-propan-2-ol; various solvent(s) / 0.33 h / 25 °C
8: 28.4 mg / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; i-Pr2NEt2 / tetrahydrofuran / 18 h / 20 °C
9: 77 percent / MTBD / dimethylformamide / 1.5 h / 20 °C
10: 96 percent / n-Bu4NF; AcOH / tetrahydrofuran / 3 h / 20 °C
11: 74 percent / β-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C
12: 85 percent / H2; aq. HCl / Pd black / ethanol / 2 h
View Scheme
参考文献
Cao, Bin; Park, Haengsoon; Joullie, Madeleine M.
Journal of the American Chemical Society, 2002 , vol. 124, # 4 p. 520 - 521
反应条件
1: 77 percent / MTBD / dimethylformamide / 1.5 h / 20 °C
2: 96 percent / n-Bu4NF; AcOH / tetrahydrofuran / 3 h / 20 °C
3: 74 percent / β-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C
4: 85 percent / H2; aq. HCl / Pd black / ethanol / 2 h
View Scheme
参考文献
Cao, Bin; Park, Haengsoon; Joullie, Madeleine M.
Journal of the American Chemical Society, 2002 , vol. 124, # 4 p. 520 - 521
反应条件
lithium hydroxide
T=20°C;
参考文献
Tanaka, Hiroko; Sawayama, Andrew M.; Wandless, Thomas J.
Journal of the American Chemical Society, 2003 , vol. 125, # 23 p. 6864 - 6865
