<3-(benzyloxy)-4-methyl-2-nitrobenzoyl>-L-threonyl-D-valyl-L-prolyl-sarcosyl-N-methyl-L-valine lactone

Base Information

• Chemical Name: <3-(benzyloxy)-4-methyl-2-nitrobenzoyl>-L-threonyl-D-valyl-L-prolyl-sarcosyl-N-methyl-L-valine lactone
• CAS No.: 2478-48-0
• Molecular Formula: C₃₈H₅₀N₆O₁₀
• Molecular Weight: 750.849
• Mol file: 2478-48-0.mol

Synonyms:<3-(benzyloxy)-4-methyl-2-nitrobenzoyl>-L-threonyl-D-valyl-L-prolyl-sarcosyl-N-methyl-L-valine lactone

Chemical Property of <3-(benzyloxy)-4-methyl-2-nitrobenzoyl>-L-threonyl-D-valyl-L-prolyl-sarcosyl-N-methyl-L-valine lactone

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3-(benzyloxy)-4-methyl-2-nitrobenzoyl>-L-threonyl-D-valyl-L-prolyl-sarcosyl-N-methyl-L-valine lactone

There total 16 articles about <3-(benzyloxy)-4-methyl-2-nitrobenzoyl>-L-threonyl-D-valyl-L-prolyl-sarcosyl-N-methyl-L-valine 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:

H-D-Val-Pro-Sar-OBut (5616-83-1) → <3-(benzyloxy)-4-methyl-2-nitrobenzoyl>-L-threonyl-D-valyl-L-prolyl-sarcosyl-N-methyl-L-valine lactone (2478-48-0)

Guidance literature:

Multi-step reaction with 6 steps

1: DCC / CH₂Cl₂ / -10 °C

2: 82 percent / N,N-(dimethylamino)pyridine, DCC / CH₂Cl₂ / -10 °C / 1.) 0 deg C, 2 h, 2.) RT, 12 h

3: 4 h / 0 °C

4: triethylamine, N,N-(bis(2-oxo-3-oxazolidinyl)phosphorodiamidic chloride / CH₂Cl₂ / 120 h / 23 °C

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

6: DCC / CH₂Cl₂ / 1.) 0 deg C, 3 h, 2.) RT, overnight

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

DOI:10.1021/ja00085a002

Reference yield:

N-(benzyloxycarbonyl)-D-valylprolylsarcosine tert-butyl ester (27483-27-8) → <3-(benzyloxy)-4-methyl-2-nitrobenzoyl>-L-threonyl-D-valyl-L-prolyl-sarcosyl-N-methyl-L-valine lactone (2478-48-0)

Guidance literature:

Multi-step reaction with 7 steps

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

2: DCC / CH₂Cl₂ / -10 °C

3: 82 percent / N,N-(dimethylamino)pyridine, DCC / CH₂Cl₂ / -10 °C / 1.) 0 deg C, 2 h, 2.) RT, 12 h

4: 4 h / 0 °C

5: triethylamine, N,N-(bis(2-oxo-3-oxazolidinyl)phosphorodiamidic chloride / CH₂Cl₂ / 120 h / 23 °C

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

7: DCC / CH₂Cl₂ / 1.) 0 deg C, 3 h, 2.) RT, overnight

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

DOI:10.1021/ja00085a002

Reference yield:

N-(benzyloxycarbonyl)threonyl-D-valylprolylsarcosyl-N-methylvaline lactone → <3-(benzyloxy)-4-methyl-2-nitrobenzoyl>-L-threonyl-D-valyl-L-prolyl-sarcosyl-N-methyl-L-valine lactone (2478-48-0)

Guidance literature:

Multi-step reaction with 2 steps

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

2: DCC / CH₂Cl₂ / 1.) 0 deg C, 3 h, 2.) RT, overnight

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

DOI:10.1021/ja00085a002

upstream raw materials:

2-nitro-3-benzyloxy-4-methylbenzoyl chloride

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

(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-butyric acid (1R,2S)-2-(3-benzyloxy-4-methyl-2-nitro-benzoylamino)-2-{(R)-1-[(S)-2-(carboxymethyl-methyl-carbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propylcarbamoyl}-1-methyl-ethyl ester

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

Downstream raw materials:

(3-hydroxy-4-methyl-2-nitrobenzoyl)-L-threonyl-D-valyl-L-prolyl-sarcosyl-N-methyl-L-valine lactone

actinomycin D