3-[4-((S)-2-Amino-2-carboxy-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid methyl ester

Base Information

• Chemical Name: 3-[4-((S)-2-Amino-2-carboxy-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid methyl ester
• CAS No.: 460322-88-7
• Molecular Formula: C₃₁H₂₈NO₅P
• Molecular Weight: 525.541

Synonyms:3-[4-((S)-2-Amino-2-carboxy-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid methyl ester

Chemical Property of 3-[4-((S)-2-Amino-2-carboxy-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid methyl ester

Chemical Property:

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Technology Process of 3-[4-((S)-2-Amino-2-carboxy-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid methyl ester

There total 6 articles about 3-[4-((S)-2-Amino-2-carboxy-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid methyl 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:

3-[4-(2-tert-butoxycarbonylamino-2-carboxy-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ5-phosphanylidene)-propionic acid methyl ester → 3-[4-((S)-2-Amino-2-carboxy-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ5-phosphanylidene)-propionic acid methyl ester (460322-88-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/S0960-894X(01)00269-4

Reference yield:

N-tert.-butoxycarbonyl-(4-trifluoromethanesulfonyloxy)-L-phenylalanine benzyl ester (123993-20-4) → 3-[4-((S)-2-Amino-2-carboxy-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ5-phosphanylidene)-propionic acid methyl ester (460322-88-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / Pd(OAc)2; dppp; Et₃N / dimethylsulfoxide / 2 h / 80 °C

2: 80 percent / Bu₄NF / tetrahydrofuran / 5 h / 20 °C

3: 42 percent / EDC; DMAP / tetrahydrofuran / 28 h / 20 °C

4: H₂ / Pd/C / methanol / 0.5 h / 20 °C

5: TFA / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; palladium diacetate; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0960-894X(01)00269-4

Reference yield:

4-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-benzoic acid (150618-07-8) → 3-[4-((S)-2-Amino-2-carboxy-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ5-phosphanylidene)-propionic acid methyl ester (460322-88-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 42 percent / EDC; DMAP / tetrahydrofuran / 28 h / 20 °C

2: H₂ / Pd/C / methanol / 0.5 h / 20 °C

3: TFA / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0960-894X(01)00269-4

upstream raw materials:

4-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-benzoic acid

N-tert.-butoxycarbonyl-(4-trifluoromethanesulfonyloxy)-L-phenylalanine benzyl ester

4-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-benzoic acid 2-trimethylsilanyl-ethyl ester

methyl (triphenylphosphoranylidene)acetate

Downstream raw materials:

3-[4-((S)-2-Acetylamino-2-carboxy-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid methyl ester

(S)-4-{(S)-2-Acetylamino-3-[4-(2-methoxycarbonyl-2-oxo-acetyl)-phenyl]-propionylamino}-4-[(1S,2R)-1-((S)-1-carbamoyl-3-methyl-butylcarbamoyl)-2-hydroxy-propylcarbamoyl]-butyric acid benzyl ester

(S)-4-{(S)-2-Acetylamino-3-[4-(2-methoxycarbonyl-2-oxo-acetyl)-phenyl]-propionylamino}-4-[(S)-3-tert-butoxycarbonyl-1-((1S,2S)-1-carbamoyl-2-methyl-butylcarbamoyl)-propylcarbamoyl]-butyric acid tert-butyl ester

(S)-4-((S)-2-Acetylamino-3-{4-[2-methoxycarbonyl-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-phenyl}-propionylamino)-4-[(1S,2R)-1-((S)-1-carbamoyl-3-methyl-butylcarbamoyl)-2-hydroxy-propylcarbamoyl]-butyric acid benzyl ester

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