N-Boc-D-AlaThz-Trp-(4-OMe)Trp-Gly-D-Abu-(Ph)Sec-Sar-OEt

Base Information

• Chemical Name: N-Boc-D-AlaThz-Trp-(4-OMe)Trp-Gly-D-Abu-(Ph)Sec-Sar-OEt
• CAS No.: 406938-58-7
• Molecular Formula: C₅₄H₆₆N₁₀O₁₁SSe
• Molecular Weight: 1142.2
• Mol file: 406938-58-7.mol

Synonyms:N-Boc-D-AlaThz-Trp-(4-OMe)Trp-Gly-D-Abu-(Ph)Sec-Sar-OEt

Chemical Property of N-Boc-D-AlaThz-Trp-(4-OMe)Trp-Gly-D-Abu-(Ph)Sec-Sar-OEt

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-Boc-D-AlaThz-Trp-(4-OMe)Trp-Gly-D-Abu-(Ph)Sec-Sar-OEt

There total 22 articles about N-Boc-D-AlaThz-Trp-(4-OMe)Trp-Gly-D-Abu-(Ph)Sec-Sar-OEt which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-methoxy-L-tryptophan (406938-53-2,199540-73-3) → N-Boc-D-AlaThz-Trp-(4-OMe)Trp-Gly-D-Abu-(Ph)Sec-Sar-OEt (406938-58-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 0.376 g / NaHCO₃; NaOH / tetrahydrofuran; H₂O / 20 °C / pH 7

2: 94 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; diisopropylethylamine / CH₂Cl₂ / 2 h / 20 °C

3: H₂; aq. HCl / 10 percent Pd/C / methanol / 4 h / 20 °C

4: 342 mg / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; diisopropylethylamine / CH₂Cl₂ / 2 h / 20 °C

5: H₂ / 10 percent Pd/C / methanol / 2 h / 20 °C

6: 186 mg / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole / CH₂Cl₂ / 2 h / 20 °C

7: LiOH / tetrahydrofuran; methanol; H₂O / 1.5 h / 20 °C

8: 185 mg / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; diisopropylethylamine / CH₂Cl₂ / 1.5 h / 20 °C

With hydrogenchloride; lithium hydroxide; sodium hydroxide; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1002/1099-0690(200212)2002:23<3995::AID-EJOC3995>3.0.CO;2-P

Reference yield:

(4-OMe)Trp-Gly-OMe (1026562-22-0) → N-Boc-D-AlaThz-Trp-(4-OMe)Trp-Gly-D-Abu-(Ph)Sec-Sar-OEt (406938-58-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 342 mg / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; diisopropylethylamine / CH₂Cl₂ / 2 h / 20 °C

2: H₂ / 10 percent Pd/C / methanol / 2 h / 20 °C

3: 186 mg / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole / CH₂Cl₂ / 2 h / 20 °C

4: LiOH / tetrahydrofuran; methanol; H₂O / 1.5 h / 20 °C

5: 185 mg / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; diisopropylethylamine / CH₂Cl₂ / 1.5 h / 20 °C

With lithium hydroxide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1002/1099-0690(200212)2002:23<3995::AID-EJOC3995>3.0.CO;2-P

Reference yield:

3-(4-methoxy-1H-indol-3-yl)-2-phenylacetylaminopropionic acid (406938-52-1) → N-Boc-D-AlaThz-Trp-(4-OMe)Trp-Gly-D-Abu-(Ph)Sec-Sar-OEt (406938-58-7)

Guidance literature:

Multi-step reaction with 9 steps

1: NaOH; penicillin G acylase / methanol; H₂O / 20 °C / pH 7.6

2: 0.376 g / NaHCO₃; NaOH / tetrahydrofuran; H₂O / 20 °C / pH 7

3: 94 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; diisopropylethylamine / CH₂Cl₂ / 2 h / 20 °C

4: H₂; aq. HCl / 10 percent Pd/C / methanol / 4 h / 20 °C

5: 342 mg / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; diisopropylethylamine / CH₂Cl₂ / 2 h / 20 °C

6: H₂ / 10 percent Pd/C / methanol / 2 h / 20 °C

7: 186 mg / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole / CH₂Cl₂ / 2 h / 20 °C

8: LiOH / tetrahydrofuran; methanol; H₂O / 1.5 h / 20 °C

9: 185 mg / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; diisopropylethylamine / CH₂Cl₂ / 1.5 h / 20 °C

With hydrogenchloride; lithium hydroxide; sodium hydroxide; penicillin G acylase; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1002/1099-0690(200212)2002:23<3995::AID-EJOC3995>3.0.CO;2-P

upstream raw materials:

D-Abu-(Ph)Sec-Sar-OEt

4-methoxy-1H-indole

(4-methoxy-1H-indol-3-ylmethyl)dimethylamine

Boc-(R)-Ala

Downstream raw materials:

Cyclo[D-AlaThz-L-Trp-L-(4-OMe)Trp-Gly-D-Aby-L-(Ph)Sec-Sar]