methyl N-(benzyloxycarbonyl)glycyl-L-phenylalanyl-D-prolyl-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropanoate

Base Information

• Chemical Name: methyl N-(benzyloxycarbonyl)glycyl-L-phenylalanyl-D-prolyl-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropanoate
• CAS No.: 77087-64-0
• Molecular Formula: C₃₃H₄₃N₅O₉
• Molecular Weight: 653.733
• Mol file: 77087-64-0.mol

Synonyms:methyl N-(benzyloxycarbonyl)glycyl-L-phenylalanyl-D-prolyl-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropanoate

Chemical Property of methyl N-(benzyloxycarbonyl)glycyl-L-phenylalanyl-D-prolyl-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl N-(benzyloxycarbonyl)glycyl-L-phenylalanyl-D-prolyl-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropanoate

There total 6 articles about methyl N-(benzyloxycarbonyl)glycyl-L-phenylalanyl-D-prolyl-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropanoate 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: 72.0%

Z-Gly-L-Phe-D-Pro-OH (77087-62-8) + methyl (S)-2-amino-3-tert-butoxycarbonylaminopropanoate (77087-60-6,161972-25-4) → methyl N-(benzyloxycarbonyl)glycyl-L-phenylalanyl-D-prolyl-Nβ-(tert-butoxycarbonyl)-L-α,β-diaminopropanoate (77087-64-0)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 4 ℃;

DOI:10.1021/jm00137a017

Reference yield:

N-(tert-butyloxycarbonyl) azide (1070-19-5) → methyl N-(benzyloxycarbonyl)glycyl-L-phenylalanyl-D-prolyl-Nβ-(tert-butoxycarbonyl)-L-α,β-diaminopropanoate (77087-64-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 88.4 percent / 1 N aq. NaoH / dioxane / 48 h / 45 °C

2: Na, NH₃(liq.) / 0.17 h / -50 °C

3: 61 percent / 4 N aq. NaOH / 2 h / 25 °C / pH 10-10.5

4: 79.5 percent / diethyl ether

5: 100 percent / H₂ / 10percent Pd/C / methanol / 24 h

6: 72 percent / DCC, HOBt / CH₂Cl₂ / 4 °C

With sodium hydroxide; ammonia; hydrogen; sodium; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jm00137a017

Reference yield:

methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]propanoate (58457-98-0) → methyl N-(benzyloxycarbonyl)glycyl-L-phenylalanyl-D-prolyl-Nβ-(tert-butoxycarbonyl)-L-α,β-diaminopropanoate (77087-64-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / 10percent Pd/C / methanol / 24 h

2: 72 percent / DCC, HOBt / CH₂Cl₂ / 4 °C

With hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/jm00137a017

upstream raw materials:

Z-Gly-L-Phe-D-Pro-OH

methyl (S)-2-amino-3-tert-butoxycarbonylaminopropanoate

N-(tert-butyloxycarbonyl) azide

N-[(benzyloxy)carbonyl]-3-[(tert-butoxycarbonyl)amino]-L-alanine

Downstream raw materials:

cyclo(glycyl-L-phenylalanyl-D-prolyl-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropanoyl)

cyclo(glycyl-L-phenylalanyl-D-prolyl-N^β-(N-maleoylglycyl)-L-α,β-diaminopropanoyl)

(S)-2-({(R)-1-[(S)-2-(2-Amino-acetylamino)-3-phenyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-tert-butoxycarbonylamino-propionic acid 2,4,5-trichloro-phenyl ester

(S)-2-({(R)-1-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-phenyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-tert-butoxycarbonylamino-propionic acid 2,4,5-trichloro-phenyl ester