(3-(benzyloxy)-4-methyl-2-nitrobenzoyl)threonyl-D-phenylalaninylprolylsarcosyl-N-methylvaline lactone

Base Information

• Chemical Name: (3-(benzyloxy)-4-methyl-2-nitrobenzoyl)threonyl-D-phenylalaninylprolylsarcosyl-N-methylvaline lactone
• CAS No.: 158680-41-2
• Molecular Formula: C₄₂H₅₀N₆O₁₀
• Molecular Weight: 798.893
• Mol file: 158680-41-2.mol

Synonyms:(3-(benzyloxy)-4-methyl-2-nitrobenzoyl)threonyl-D-phenylalaninylprolylsarcosyl-N-methylvaline lactone

Chemical Property of (3-(benzyloxy)-4-methyl-2-nitrobenzoyl)threonyl-D-phenylalaninylprolylsarcosyl-N-methylvaline lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3-(benzyloxy)-4-methyl-2-nitrobenzoyl)threonyl-D-phenylalaninylprolylsarcosyl-N-methylvaline lactone

There total 8 articles about (3-(benzyloxy)-4-methyl-2-nitrobenzoyl)threonyl-D-phenylalaninylprolylsarcosyl-N-methylvaline lactone 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:

[Methyl-((S)-pyrrolidine-2-carbonyl)-amino]-acetic acid tert-butyl ester (63219-23-8) → (3-(benzyloxy)-4-methyl-2-nitrobenzoyl)threonyl-D-phenylalaninylprolylsarcosyl-N-methylvaline lactone (158680-41-2)

Guidance literature:

Multi-step reaction with 7 steps

1: dicyclohexylcarbodiimide / CH₂Cl₂ / 3 h / -10 °C

2: H₂ / 10percent Pd/C / methanol / 2 h / 760 Torr

3: dicyclohexylcarbodiimide / CH₂Cl₂ / 3 h / -10 °C

4: 93 percent / 4-(N,N-dimethylamino)pyridine, dicyclohexylcarbodiimide / CH₂Cl₂ / 14 h / 0 - 20 °C

5: 1.) trifluoroacetic acid, 2.) N,N-bis(2-oxo-3-oxazolidinyl)phosphorodiamidic chloride, triethylamine / 1.) 0 deg C, 4 h, 2.) CH₂Cl₂, RT, 5 d

6: H₂ / 10percent Pd/C / methanol / 2 h / 760 Torr

7: dicyclohexylcarbodiimide / CH₂Cl₂ / 3 h / -10 °C

With dmap; N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; hydrogen; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja00097a003

Reference yield:

N-(benzyloxycarbonyl)prolylsarcosine tert-butyl ester (5616-82-0) → (3-(benzyloxy)-4-methyl-2-nitrobenzoyl)threonyl-D-phenylalaninylprolylsarcosyl-N-methylvaline lactone (158680-41-2)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂ / 10percent Pd/C / methanol / 2 h / 760 Torr

2: dicyclohexylcarbodiimide / CH₂Cl₂ / 3 h / -10 °C

3: H₂ / 10percent Pd/C / methanol / 2 h / 760 Torr

4: dicyclohexylcarbodiimide / CH₂Cl₂ / 3 h / -10 °C

5: 93 percent / 4-(N,N-dimethylamino)pyridine, dicyclohexylcarbodiimide / CH₂Cl₂ / 14 h / 0 - 20 °C

6: 1.) trifluoroacetic acid, 2.) N,N-bis(2-oxo-3-oxazolidinyl)phosphorodiamidic chloride, triethylamine / 1.) 0 deg C, 4 h, 2.) CH₂Cl₂, RT, 5 d

7: H₂ / 10percent Pd/C / methanol / 2 h / 760 Torr

8: dicyclohexylcarbodiimide / CH₂Cl₂ / 3 h / -10 °C

With dmap; N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; hydrogen; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja00097a003

Reference yield:

{[(S)-1-((R)-2-Amino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-methyl-amino}-acetic acid tert-butyl ester → (3-(benzyloxy)-4-methyl-2-nitrobenzoyl)threonyl-D-phenylalaninylprolylsarcosyl-N-methylvaline lactone (158680-41-2)

Guidance literature:

Multi-step reaction with 5 steps

1: dicyclohexylcarbodiimide / CH₂Cl₂ / 3 h / -10 °C

2: 93 percent / 4-(N,N-dimethylamino)pyridine, dicyclohexylcarbodiimide / CH₂Cl₂ / 14 h / 0 - 20 °C

3: 1.) trifluoroacetic acid, 2.) N,N-bis(2-oxo-3-oxazolidinyl)phosphorodiamidic chloride, triethylamine / 1.) 0 deg C, 4 h, 2.) CH₂Cl₂, RT, 5 d

4: H₂ / 10percent Pd/C / methanol / 2 h / 760 Torr

5: dicyclohexylcarbodiimide / CH₂Cl₂ / 3 h / -10 °C

With dmap; N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; hydrogen; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja00097a003

upstream raw materials:

2-nitro-3-benzyloxy-4-methylbenzoic acid N-hydroxysuccinimide ester

[Methyl-((S)-pyrrolidine-2-carbonyl)-amino]-acetic acid tert-butyl ester

N-(benzyloxycarbonyl)prolylsarcosine tert-butyl ester

N-(benzyloxycarbonyl)-D-phenylalaninylprolylsarcosine tert-butyl ester