(2S,3R)-2-{(S)-2-[(S)-2-Amino-3-(4-methoxy-benzyloxycarbonyl)-propionylamino]-4-methyl-pentanoylamino}-3-benzyloxy-butyric acid allyl ester

Base Information

• Chemical Name: (2S,3R)-2-{(S)-2-[(S)-2-Amino-3-(4-methoxy-benzyloxycarbonyl)-propionylamino]-4-methyl-pentanoylamino}-3-benzyloxy-butyric acid allyl ester
• CAS No.: 167414-34-8
• Molecular Formula: C₃₂H₄₃N₃O₈
• Molecular Weight: 597.709
• Mol file: 167414-34-8.mol

Synonyms:(2S,3R)-2-{(S)-2-[(S)-2-Amino-3-(4-methoxy-benzyloxycarbonyl)-propionylamino]-4-methyl-pentanoylamino}-3-benzyloxy-butyric acid allyl ester

Chemical Property of (2S,3R)-2-{(S)-2-[(S)-2-Amino-3-(4-methoxy-benzyloxycarbonyl)-propionylamino]-4-methyl-pentanoylamino}-3-benzyloxy-butyric acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-{(S)-2-[(S)-2-Amino-3-(4-methoxy-benzyloxycarbonyl)-propionylamino]-4-methyl-pentanoylamino}-3-benzyloxy-butyric acid allyl ester

There total 5 articles about (2S,3R)-2-{(S)-2-[(S)-2-Amino-3-(4-methoxy-benzyloxycarbonyl)-propionylamino]-4-methyl-pentanoylamino}-3-benzyloxy-butyric acid allyl 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:

L-Asparaginsaeure-4-(4-methoxy-benzylester) (3940-66-7) → (2S,3R)-2-{(S)-2-[(S)-2-Amino-3-(4-methoxy-benzyloxycarbonyl)-propionylamino]-4-methyl-pentanoylamino}-3-benzyloxy-butyric acid allyl ester (167414-34-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaOH, aq. NaHCO₃ / 2.) dioxane

2: 73 percent / EDACI, NMM, HOBt / dimethylformamide; CH₂Cl₂

3: Pd(PPh₃)4, morpholine / tetrahydrofuran

4: IIDQ / CH₂Cl₂

5: Zn, AcOH

With morpholine; 4-methyl-morpholine; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja9740071

Reference yield:

(S)-2-(2,2,2-Trichloro-ethoxycarbonylamino)-succinic acid 4-(4-methoxy-benzyl) ester (143918-05-2) → (2S,3R)-2-{(S)-2-[(S)-2-Amino-3-(4-methoxy-benzyloxycarbonyl)-propionylamino]-4-methyl-pentanoylamino}-3-benzyloxy-butyric acid allyl ester (167414-34-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 73 percent / EDACI, NMM, HOBt / dimethylformamide; CH₂Cl₂

2: Pd(PPh₃)4, morpholine / tetrahydrofuran

3: IIDQ / CH₂Cl₂

4: Zn, AcOH

With morpholine; 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja9740071

Reference yield:

(S)-2-[(S)-3-(4-Methoxy-benzyloxycarbonyl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionylamino]-4-methyl-pentanoic acid (186504-27-8) → (2S,3R)-2-{(S)-2-[(S)-2-Amino-3-(4-methoxy-benzyloxycarbonyl)-propionylamino]-4-methyl-pentanoylamino}-3-benzyloxy-butyric acid allyl ester (167414-34-8)

Guidance literature:

Multi-step reaction with 2 steps

1: IIDQ / CH₂Cl₂

2: Zn, AcOH

With 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline; acetic acid; zinc; In dichloromethane;

DOI:10.1021/ja9740071

upstream raw materials:

(2S,3R)-3-Benzyloxy-2-{(S)-2-[(S)-3-(4-methoxy-benzyloxycarbonyl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionylamino]-4-methyl-pentanoylamino}-butyric acid allyl ester

L-Asparaginsaeure-4-(4-methoxy-benzylester)

(S)-2-(2,2,2-Trichloro-ethoxycarbonylamino)-succinic acid 4-(4-methoxy-benzyl) ester

(S)-2-[(S)-3-(4-Methoxy-benzyloxycarbonyl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionylamino]-4-methyl-pentanoic acid

Downstream raw materials:

(2S,3R)-3-Benzyloxy-2-((S)-2-{(S)-2-[(S)-2-((S)-2-benzyloxycarbonylamino-propionylamino)-4-methyl-pentanoylamino]-3-carboxy-propionylamino}-4-methyl-pentanoylamino)-butyric acid allyl ester

(2S,3R)-3-Benzyloxy-2-{(S)-2-[(S)-2-[(S)-2-((S)-2-benzyloxycarbonylamino-propionylamino)-4-methyl-pentanoylamino]-3-(4-methoxy-benzyloxycarbonyl)-propionylamino]-4-methyl-pentanoylamino}-butyric acid allyl ester