(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

Base Information

• Chemical Name: (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
• CAS No.: 98757-23-4
• Molecular Formula: C₄₃H₆₀N₆O₁₃
• Molecular Weight: 868.982
• Mol file: 98757-23-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 5 articles about (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 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:

N-<3-(benzyloxy)-4-methyl-2-nitrobenzoyl>-O-(tert-butoxycarbonyl-N-methyl-L-valyl)-L-threonyl-D-valyl-L-prolylsarcosine ter-butyl ester (98688-14-3) → (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 (98757-23-4)

Guidance literature:

With hydrogenchloride; sodium hydroxide; In 1,4-dioxane; at 22 ℃; for 2h;

DOI:10.1021/ja00310a065

Reference yield:

N-(benzyloxycarbonyl)-D-valylprolylsarcosine tert-butyl ester (27483-27-8) → (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 (98757-23-4)

Guidance literature:

Multi-step reaction with 4 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

With hydrogenchloride; dmap; sodium hydroxide; cyclohexa-1,4-diene; 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) → (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 (98757-23-4)

Guidance literature:

Multi-step reaction with 3 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

With hydrogenchloride; dmap; sodium hydroxide; 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:

N-<3-(benzyloxy)-4-methyl-2-nitrobenzoyl>-O-(tert-butoxycarbonyl-N-methyl-L-valyl)-L-threonyl-D-valyl-L-prolylsarcosine ter-butyl ester

<3-(benzyloxy)-4-methyl-2-nitro-benzoyl>-L-threonine

<3-(benzyloxy)-4-methyl-2-nitrobenzoyl>-L-threonyl-D-valyl-L-prolyl-sarcosine tert-butyl ester

H-D-Val-Pro-Sar-OBu^t

Downstream raw materials:

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

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

actinomycin D