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

Base Information

• Chemical Name: (3-hydroxy-4-methyl-2-nitrobenzoyl)-L-threonyl-D-valyl-L-prolyl-sarcosyl-N-methyl-L-valine lactone
• CAS No.: 21148-64-1
• Molecular Formula: C₃₁H₄₄N₆O₁₀
• Molecular Weight: 660.725
• Mol file: 21148-64-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 30 articles about (3-hydroxy-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: 94.0%

<3-(benzyloxy)-4-methyl-2-nitrobenzoyl>-L-threonyl-D-valyl-L-prolyl-sarcosyl-N-methyl-L-valine lactone (2478-48-0) → (3-hydroxy-4-methyl-2-nitrobenzoyl)-L-threonyl-D-valyl-L-prolyl-sarcosyl-N-methyl-L-valine lactone (21148-64-1)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 23 ℃; for 0.166667h;

DOI:10.1021/ja00310a065

Reference yield:

N-(benzyloxycarbonyl)-D-valylprolylsarcosine tert-butyl ester (27483-27-8) → (3-hydroxy-4-methyl-2-nitrobenzoyl)-L-threonyl-D-valyl-L-prolyl-sarcosyl-N-methyl-L-valine lactone (21148-64-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1,4-cyclohexadiene / 10percent palladium/charcoal / ethanol

2: HONB/DCC / dimethylformamide / 48 h / -5 °C

3: 89 percent / DMAP/DCC / CH₂Cl₂ / 16 h / 26 °C

4: 1.) 4N HCl, 2.) aq. sodium hydroxide / dioxane / 2 h / 22 °C

5: diisopropylethylamine, BOP-Cl / CH₂Cl₂ / 72 h / 22 °C

6: 94 percent / trifluoromethane-sulfonic acid / CH₂Cl₂ / 0.17 h / 23 °C

With hydrogenchloride; dmap; sodium hydroxide; trifluorormethanesulfonic acid; cyclohexa-1,4-diene; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; (3aR,4R,7S,7aS)-2-hydroxy-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (N-hydroxy-5-exo-norbornene-2,3-dicarboximide); palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00310a065

Reference yield:

<3-(benzyloxy)-4-methyl-2-nitro-benzoyl>-L-threonine (2441-62-5) → (3-hydroxy-4-methyl-2-nitrobenzoyl)-L-threonyl-D-valyl-L-prolyl-sarcosyl-N-methyl-L-valine lactone (21148-64-1)

Guidance literature:

Multi-step reaction with 5 steps

1: HONB/DCC / dimethylformamide / 48 h / -5 °C

2: 89 percent / DMAP/DCC / CH₂Cl₂ / 16 h / 26 °C

3: 1.) 4N HCl, 2.) aq. sodium hydroxide / dioxane / 2 h / 22 °C

4: diisopropylethylamine, BOP-Cl / CH₂Cl₂ / 72 h / 22 °C

5: 94 percent / trifluoromethane-sulfonic acid / CH₂Cl₂ / 0.17 h / 23 °C

With hydrogenchloride; dmap; sodium hydroxide; trifluorormethanesulfonic acid; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; (3aR,4R,7S,7aS)-2-hydroxy-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (N-hydroxy-5-exo-norbornene-2,3-dicarboximide); In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00310a065

upstream raw materials:

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

N-[(benzyloxy)carbonyl]-D-valine

N-Methyl-(S)-valin-tert-butylester

benzyloxycarbonylsarcosyl-N-methylvaline t-butyl ester

Downstream raw materials:

actinomycin D

actinomycin D

C₆₁H₈₄N₁₂O₁₇

2,2'-D-Thr₂-actinomycin D