N^α-t-butoxycarbonyl-β-benzyl-L-aspartyl-L-valyl-L-tyrosine benzyl ester

Base Information

• Chemical Name: N^α-t-butoxycarbonyl-β-benzyl-L-aspartyl-L-valyl-L-tyrosine benzyl ester
• CAS No.: 75957-54-9
• Molecular Formula: C₃₇H₄₅N₃O₉
• Molecular Weight: 675.779
• Mol file: 75957-54-9.mol

Synonyms:N^α-t-butoxycarbonyl-β-benzyl-L-aspartyl-L-valyl-L-tyrosine benzyl ester

Chemical Property of N^α-t-butoxycarbonyl-β-benzyl-L-aspartyl-L-valyl-L-tyrosine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N^α-t-butoxycarbonyl-β-benzyl-L-aspartyl-L-valyl-L-tyrosine benzyl ester

There total 8 articles about N^α-t-butoxycarbonyl-β-benzyl-L-aspartyl-L-valyl-L-tyrosine benzyl ester 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: 82.0%

2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester (30925-18-9) + Val-Tyr-OBzl hydrochloride → Nα-t-butoxycarbonyl-β-benzyl-L-aspartyl-L-valyl-L-tyrosine benzyl ester (75957-54-9)

Guidance literature:

2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester; With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 ℃; for 0.5h;

Val-Tyr-OBzl hydrochloride; With 4-methyl-morpholine; In tetrahydrofuran; at 20 ℃; for 8h; pH=9;

DOI:10.1039/c5tb01930c

Reference yield:

L-tyrosine benzyl ester p-toluenesulfonate (53587-11-4,97984-63-9) → Nα-t-butoxycarbonyl-β-benzyl-L-aspartyl-L-valyl-L-tyrosine benzyl ester (75957-54-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / Et₃N / dimethylformamide / 24 h / 20 °C

2: TFA / CH₂Cl₂ / 1 h / 20 °C

3: N-ethylmorpholine / dimethylformamide / 24 h / 20 °C

With N-ethylmorpholine;; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Hydrolysis / 3: Condensation;

Reference yield:

N-[N-(tert-butoxycarbonyl)-L-valyl]-L-tyrosine benzyl ester (75957-53-8) → Nα-t-butoxycarbonyl-β-benzyl-L-aspartyl-L-valyl-L-tyrosine benzyl ester (75957-54-9)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / CH₂Cl₂ / 1 h / 20 °C

2: N-ethylmorpholine / dimethylformamide / 24 h / 20 °C

With N-ethylmorpholine;; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; 1: Hydrolysis / 2: Condensation;

upstream raw materials:

BOC-L-aspartic acid 4-benzyl ester

H-Val-Tyr-OBzl

H-Val-Tyr-OBzl*TFA

N^α-t-butoxycarbonylaspartic acid α-N-hydroxysuccinimide ester β-benzyl ester

Downstream raw materials:

Aspartyl-valyl-tyrosine

H-Asp(OBzl)-Val-Tyr-OBzl

(S)-3-Amino-N-{(S)-1-[(S)-1-benzyloxycarbonyl-2-(4-hydroxy-phenyl)-ethylcarbamoyl]-2-methyl-propyl}-succinamic acid benzyl ester; compound with trifluoro-acetic acid

2>-thymopentin (Arg-Pro-Asp-Val-Tyr)