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
hydrogenchloride; hydrogen; palladium in ethanol
2 h;
参考文献
Li, Pixu; Evans, Cory D.; Wu, Yongzhong; Cao, Bin; Hamel, Ernest; Joullie, Madeleine M.
Journal of the American Chemical Society, 2008 , vol. 130, # 7 p. 2351 - 2364
反应条件
triethylsilane; trifluoroacetic acid in dichloromethane
参考文献
Li, Pixu; Evans, Cory D.; Wu, Yongzhong; Cao, Bin; Hamel, Ernest; Joullie, Madeleine M.
Journal of the American Chemical Society, 2008 , vol. 130, # 7 p. 2351 - 2364
反应条件
1.1: 99 percent / AgSbF6; [(S)-2,2'-bis(2-OH-3,5-di-tBu-C6H2-CH=N)-1,1'-biNaphth]Al
2.1: 95 percent / K2CO3; MeOH / tetrahydrofuran
3.1: 70 percent / Pd2(dba)3*CHCl3; (S,S)-1,2-bis(2-Ph2P-C6H4-CONH)cyclohexane
4.1: 72 percent / K2OsO4*H2O; (DHQD)2PYR
5.1: TEMPO; NaOCl
6.1: NaClO2
7.1: 95 percent / BOP
8.1: LiN3
9.1: PMe3
10.1: BOP
11.2: NaBH4
12.1: (COOOH)2
13.1: LiOH / 0 °C
14.1: TFA / CH2Cl2 / 0 °C
15.1: 56 percent / PyAOP; Hunig's base
16.1: H2 / Pd/C
17.1: LiOH / 20 °C
View Scheme
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
反应条件
1.1: 99 percent / AgSbF6; [(S)-2,2'-bis(2-OH-3,5-di-tBu-C6H2-CH=N)-1,1'-biNaphth]Al
2.1: 95 percent / K2CO3; MeOH / tetrahydrofuran
3.1: 70 percent / Pd2(dba)3*CHCl3; (S,S)-1,2-bis(2-Ph2P-C6H4-CONH)cyclohexane
4.1: 72 percent / K2OsO4*H2O; (DHQD)2PYR
5.1: TEMPO; NaOCl
6.1: NaClO2
7.1: 95 percent / BOP
8.1: LiN3
9.1: PMe3
10.1: BOP
11.2: NaBH4
12.1: (COOOH)2
13.1: LiOH / 0 °C
14.1: TFA / CH2Cl2 / 0 °C
15.1: 56 percent / PyAOP; Hunig's base
16.1: H2 / Pd/C
17.1: LiOH / 20 °C
View Scheme
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
反应条件
1.1: NaOH
2.1: 99 percent / AgSbF6; [(S)-2,2'-bis(2-OH-3,5-di-tBu-C6H2-CH=N)-1,1'-biNaphth]Al
3.1: 95 percent / K2CO3; MeOH / tetrahydrofuran
4.1: 70 percent / Pd2(dba)3*CHCl3; (S,S)-1,2-bis(2-Ph2P-C6H4-CONH)cyclohexane
5.1: 72 percent / K2OsO4*H2O; (DHQD)2PYR
6.1: TEMPO; NaOCl
7.1: NaClO2
8.1: 95 percent / BOP
9.1: LiN3
10.1: PMe3
11.1: BOP
12.2: NaBH4
13.1: (COOOH)2
14.1: LiOH / 0 °C
15.1: TFA / CH2Cl2 / 0 °C
16.1: 56 percent / PyAOP; Hunig's base
17.1: H2 / Pd/C
18.1: LiOH / 20 °C
View Scheme
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
反应条件
1.1: 70 percent / Pd2(dba)3*CHCl3; (S,S)-1,2-bis(2-Ph2P-C6H4-CONH)cyclohexane
2.1: 72 percent / K2OsO4*H2O; (DHQD)2PYR
3.1: TEMPO; NaOCl
4.1: NaClO2
5.1: 95 percent / BOP
6.1: LiN3
7.1: PMe3
8.1: BOP
9.2: NaBH4
10.1: (COOOH)2
11.1: LiOH / 0 °C
12.1: TFA / CH2Cl2 / 0 °C
13.1: 56 percent / PyAOP; Hunig's base
14.1: H2 / Pd/C
15.1: LiOH / 20 °C
View Scheme
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
反应条件
1.1: 70 percent / Pd2(dba)3*CHCl3; (S,S)-1,2-bis(2-Ph2P-C6H4-CONH)cyclohexane
2.1: 72 percent / K2OsO4*H2O; (DHQD)2PYR
3.1: TEMPO; NaOCl
4.1: NaClO2
5.1: 95 percent / BOP
6.1: LiN3
7.1: PMe3
8.1: BOP
9.2: NaBH4
10.1: (COOOH)2
11.1: LiOH / 0 °C
12.1: TFA / CH2Cl2 / 0 °C
13.1: 56 percent / PyAOP; Hunig's base
14.1: H2 / Pd/C
15.1: LiOH / 20 °C
View Scheme
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
反应条件
1: 454 mg / DEBPT; i-Pr2NEt2 / tetrahydrofuran / 18 h / 20 °C
2: 2,6-lutidine / CH2Cl2 / 1 h / 20 °C
3: 143 mg / aq. LiOH / 2-methyl-propan-2-ol / 16 h / 20 °C
4: 78 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole / dimethylformamide; CH2Cl2 / 24 h / 0 - 20 °C
5: 88 percent / β-bromocatecholborane / CH2Cl2 / 0.5 h / -78 °C
6: H2; 2,2'-bipyridyl / Pd/C / methanol; ethyl acetate / 2 h
7: 37.7 mg / 2,4,6-collidine / CH2Cl2 / 3 h / 20 °C
8: Dess-Martin periodinane / CH2Cl2 / 1.25 h / 0 - 25 °C
9: aq. NaClO2; NaH2PO4*2H2O / 2-methyl-propan-2-ol; various solvent(s) / 0.33 h / 25 °C
10: 28.4 mg / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; i-Pr2NEt2 / tetrahydrofuran / 18 h / 20 °C
11: 77 percent / MTBD / dimethylformamide / 1.5 h / 20 °C
12: 96 percent / n-Bu4NF; AcOH / tetrahydrofuran / 3 h / 20 °C
13: 74 percent / β-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C
14: 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: 37.7 mg / 2,4,6-collidine / CH2Cl2 / 3 h / 20 °C
2: Dess-Martin periodinane / CH2Cl2 / 1.25 h / 0 - 25 °C
3: aq. NaClO2; NaH2PO4*2H2O / 2-methyl-propan-2-ol; various solvent(s) / 0.33 h / 25 °C
4: 28.4 mg / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; i-Pr2NEt2 / tetrahydrofuran / 18 h / 20 °C
5: 77 percent / MTBD / dimethylformamide / 1.5 h / 20 °C
6: 96 percent / n-Bu4NF; AcOH / tetrahydrofuran / 3 h / 20 °C
7: 74 percent / β-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C
8: 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: TFA / CH2Cl2 / 0.58 h / 0 °C
2: 454 mg / DEBPT; i-Pr2NEt2 / tetrahydrofuran / 18 h / 20 °C
3: 2,6-lutidine / CH2Cl2 / 1 h / 20 °C
4: 143 mg / aq. LiOH / 2-methyl-propan-2-ol / 16 h / 20 °C
5: 78 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole / dimethylformamide; CH2Cl2 / 24 h / 0 - 20 °C
6: 88 percent / β-bromocatecholborane / CH2Cl2 / 0.5 h / -78 °C
7: H2; 2,2'-bipyridyl / Pd/C / methanol; ethyl acetate / 2 h
8: 37.7 mg / 2,4,6-collidine / CH2Cl2 / 3 h / 20 °C
9: Dess-Martin periodinane / CH2Cl2 / 1.25 h / 0 - 25 °C
10: aq. NaClO2; NaH2PO4*2H2O / 2-methyl-propan-2-ol; various solvent(s) / 0.33 h / 25 °C
11: 28.4 mg / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; i-Pr2NEt2 / tetrahydrofuran / 18 h / 20 °C
12: 77 percent / MTBD / dimethylformamide / 1.5 h / 20 °C
13: 96 percent / n-Bu4NF; AcOH / tetrahydrofuran / 3 h / 20 °C
14: 74 percent / β-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C
15: 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
