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

Base Information

• Chemical Name: Cyclo[D-AlaThz-L-Trp-L-(4-OMe)Trp-Gly-D-Aby-L-(Ph)Sec-Sar]
• CAS No.: 406938-59-8
• Molecular Formula: C₄₇H₅₂N₁₀O₈SSe
• Molecular Weight: 996.018
• Mol file: 406938-59-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 23 articles about Cyclo[D-AlaThz-L-Trp-L-(4-OMe)Trp-Gly-D-Aby-L-(Ph)Sec-Sar] 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:

D-AlaThz-Trp-(4-OMe)Trp-Gly-D-Abu-(Ph)Sec-Sar-OH → Cyclo[D-AlaThz-L-Trp-L-(4-OMe)Trp-Gly-D-Aby-L-(Ph)Sec-Sar] (406938-59-8)

Guidance literature:

With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 2h;

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

Reference yield:

4-methoxy-L-tryptophan (406938-53-2,199540-73-3) → Cyclo[D-AlaThz-L-Trp-L-(4-OMe)Trp-Gly-D-Aby-L-(Ph)Sec-Sar] (406938-59-8)

Guidance literature:

Multi-step reaction with 11 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

9: LiOH / tetrahydrofuran; methanol; H₂O / 2 h / 20 °C

10: TFA / methoxybenzene / 0.33 h / 20 °C

11: 32 mg / 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium BF₄; 1-hydroxybenzotriazole; diisopropylethylamine / CH₂Cl₂ / 2 h / 20 °C

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

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) → Cyclo[D-AlaThz-L-Trp-L-(4-OMe)Trp-Gly-D-Aby-L-(Ph)Sec-Sar] (406938-59-8)

Guidance literature:

Multi-step reaction with 8 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

6: LiOH / tetrahydrofuran; methanol; H₂O / 2 h / 20 °C

7: TFA / methoxybenzene / 0.33 h / 20 °C

8: 32 mg / 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium BF₄; 1-hydroxybenzotriazole; diisopropylethylamine / CH₂Cl₂ / 2 h / 20 °C

With lithium hydroxide; hydrogen; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; methoxybenzene;

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

upstream raw materials:

4-methoxy-1H-indole

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

(R)-2-(1-((tert-butoxycarbonyl)amino)ethyl)thiazole-4-carboxylic acid

1'-(R)-2-(1-tert-butoxycarbonylaminoethyl)thiazole-4-carboxylic acid ethyl ester