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

Base Information

• Chemical Name: (S)-4-((S)-2-Acetylamino-3-{4-[2-methoxycarbonyl-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-phenyl}-propionylamino)-4-[(S)-3-tert-butoxycarbonyl-1-((1S,2S)-1-carbamoyl-2-methyl-butylcarbamoyl)-propylcarbamoyl]-butyric acid tert-butyl ester
• CAS No.: 367266-82-8
• Molecular Formula: C₅₇H₇₂N₅O₁₂P
• Molecular Weight: 1050.2

Synonyms:(S)-4-((S)-2-Acetylamino-3-{4-[2-methoxycarbonyl-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-phenyl}-propionylamino)-4-[(S)-3-tert-butoxycarbonyl-1-((1S,2S)-1-carbamoyl-2-methyl-butylcarbamoyl)-propylcarbamoyl]-butyric acid tert-butyl ester

Chemical Property of (S)-4-((S)-2-Acetylamino-3-{4-[2-methoxycarbonyl-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-phenyl}-propionylamino)-4-[(S)-3-tert-butoxycarbonyl-1-((1S,2S)-1-carbamoyl-2-methyl-butylcarbamoyl)-propylcarbamoyl]-butyric acid tert-butyl ester

Chemical Property:

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Technology Process of (S)-4-((S)-2-Acetylamino-3-{4-[2-methoxycarbonyl-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-phenyl}-propionylamino)-4-[(S)-3-tert-butoxycarbonyl-1-((1S,2S)-1-carbamoyl-2-methyl-butylcarbamoyl)-propylcarbamoyl]-butyric acid tert-butyl ester

There total 8 articles about (S)-4-((S)-2-Acetylamino-3-{4-[2-methoxycarbonyl-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-phenyl}-propionylamino)-4-[(S)-3-tert-butoxycarbonyl-1-((1S,2S)-1-carbamoyl-2-methyl-butylcarbamoyl)-propylcarbamoyl]-butyric acid tert-butyl 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: 57.0%

Glu(OtBu)-Glu(OtBu)-Ile-NH2 + 3-[4-((S)-2-Acetylamino-2-carboxy-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ5-phosphanylidene)-propionic acid methyl ester (367266-73-7) → (S)-4-((S)-2-Acetylamino-3-{4-[2-methoxycarbonyl-2-(triphenyl-λ5-phosphanylidene)-acetyl]-phenyl}-propionylamino)-4-[(S)-3-tert-butoxycarbonyl-1-((1S,2S)-1-carbamoyl-2-methyl-butylcarbamoyl)-propylcarbamoyl]-butyric acid tert-butyl ester (367266-82-8)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 4.5h;

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

Reference yield:

4-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-benzoic acid (150618-07-8) → (S)-4-((S)-2-Acetylamino-3-{4-[2-methoxycarbonyl-2-(triphenyl-λ5-phosphanylidene)-acetyl]-phenyl}-propionylamino)-4-[(S)-3-tert-butoxycarbonyl-1-((1S,2S)-1-carbamoyl-2-methyl-butylcarbamoyl)-propylcarbamoyl]-butyric acid tert-butyl ester (367266-82-8)

Guidance literature:

Multi-step reaction with 5 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

4: 81 percent / Et₃N / 1,2-dimethoxy-ethane / 18 h / 20 °C

5: 57 percent / EDC; HOBt / CH₂Cl₂; dimethylformamide / 4.5 h / 20 °C

With dmap; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

N-tert.-butoxycarbonyl-(4-trifluoromethanesulfonyloxy)-L-phenylalanine benzyl ester (123993-20-4) → (S)-4-((S)-2-Acetylamino-3-{4-[2-methoxycarbonyl-2-(triphenyl-λ5-phosphanylidene)-acetyl]-phenyl}-propionylamino)-4-[(S)-3-tert-butoxycarbonyl-1-((1S,2S)-1-carbamoyl-2-methyl-butylcarbamoyl)-propylcarbamoyl]-butyric acid tert-butyl ester (367266-82-8)

Guidance literature:

Multi-step reaction with 7 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

6: 81 percent / Et₃N / 1,2-dimethoxy-ethane / 18 h / 20 °C

7: 57 percent / EDC; HOBt / CH₂Cl₂; dimethylformamide / 4.5 h / 20 °C

With dmap; palladium diacetate; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

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

upstream raw materials:

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

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

Downstream raw materials:

(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

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