Technology Process of cyclic Pro-Gly-Val-Gly-Tyr(β-OH,4-methyl,3-(2-methylbutyl))-Gly-Trp
There total 13 articles about cyclic Pro-Gly-Val-Gly-Tyr(β-OH,4-methyl,3-(2-methylbutyl))-Gly-Trp which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
hydrogen;
palladium on activated charcoal;
In
methanol;
for 3h;
under 1551.4 Torr;
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: Na / diethyl ether
1.2: 74 percent / ZnBr2 / CH2Cl2
2.1: 93 percent / K2CO3 / acetone / Heating
3.1: 85 percent / t-BuLi / tetrahydrofuran / -78 °C
4.1: BuLi / tetrahydrofuran / -78 - -20 °C
5.1: 56 percent / TFA / H2O
6.1: H2 / Pd/C / methanol
7.1: HOBt; EDCI; DIPEA / CH2Cl2
8.1: LiOH / acetonitrile
9.1: HOBt; EDCI; DIPEA / TFA / CH2Cl2
10.1: H2 / 10 percent Pd/C / methanol
11.1: FDPP; DIPEA / dimethylformamide
With
lithium hydroxide; n-butyllithium; pentafluorophenyl diphenyl-phosphinate; hydrogen; tert.-butyl lithium; sodium; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
palladium on activated charcoal; trifluoroacetic acid;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;
1.1: Metallation / 1.2: Alkylation / 2.1: Methylation / 3.1: Carbonylation / 4.1: Addition / 5.1: Hydrolysis / 6.1: Hydrogenation / 7.1: Acylation / 8.1: Hydrolysis / 9.1: Acylation / 10.1: Hydrogenolysis / 11.1: Cyclization;
DOI:10.1016/S0040-4039(99)01930-9
- Guidance literature:
-
Multi-step reaction with 8 steps
1: BuLi / tetrahydrofuran / -78 - -20 °C
2: 56 percent / TFA / H2O
3: H2 / Pd/C / methanol
4: HOBt; EDCI; DIPEA / CH2Cl2
5: LiOH / acetonitrile
6: HOBt; EDCI; DIPEA / TFA / CH2Cl2
7: H2 / 10 percent Pd/C / methanol
8: FDPP; DIPEA / dimethylformamide
With
lithium hydroxide; n-butyllithium; pentafluorophenyl diphenyl-phosphinate; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
palladium on activated charcoal; trifluoroacetic acid;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
1: Addition / 2: Hydrolysis / 3: Hydrogenation / 4: Acylation / 5: Hydrolysis / 6: Acylation / 7: Hydrogenolysis / 8: Cyclization;
DOI:10.1016/S0040-4039(99)01930-9