(4S)-4-((1S)-1-{1-benzylcarbamoyl-1-[2-(tert-butyldiphenylsiloxy)ethyl]butylcarbamoyl}-2-phenylethylcarbamoyl)-4-(benzyloxycarbonylamino)butyric acid benzyl ester

Base Information

• Chemical Name: (4S)-4-((1S)-1-{1-benzylcarbamoyl-1-[2-(tert-butyldiphenylsiloxy)ethyl]butylcarbamoyl}-2-phenylethylcarbamoyl)-4-(benzyloxycarbonylamino)butyric acid benzyl ester
• CAS No.: 872983-57-8
• Molecular Formula: C₅₉H₆₈N₄O₈Si
• Molecular Weight: 989.296

Synonyms:(4S)-4-((1S)-1-{1-benzylcarbamoyl-1-[2-(tert-butyldiphenylsiloxy)ethyl]butylcarbamoyl}-2-phenylethylcarbamoyl)-4-(benzyloxycarbonylamino)butyric acid benzyl ester

Chemical Property of (4S)-4-((1S)-1-{1-benzylcarbamoyl-1-[2-(tert-butyldiphenylsiloxy)ethyl]butylcarbamoyl}-2-phenylethylcarbamoyl)-4-(benzyloxycarbonylamino)butyric acid benzyl ester

Chemical Property:

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Technology Process of (4S)-4-((1S)-1-{1-benzylcarbamoyl-1-[2-(tert-butyldiphenylsiloxy)ethyl]butylcarbamoyl}-2-phenylethylcarbamoyl)-4-(benzyloxycarbonylamino)butyric acid benzyl ester

There total 9 articles about (4S)-4-((1S)-1-{1-benzylcarbamoyl-1-[2-(tert-butyldiphenylsiloxy)ethyl]butylcarbamoyl}-2-phenylethylcarbamoyl)-4-(benzyloxycarbonylamino)butyric acid benzyl 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: 98.0%

2-(2-amino-3-phenyl-propionylamino)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-pentanoic acid benzylamide (872984-01-5) + N-benzyloxycarbonyl-5-O-benzyl-L-glutamic acid (5680-86-4) → (4S)-4-((1S)-1-{1-benzylcarbamoyl-1-[2-(tert-butyldiphenylsiloxy)ethyl]butylcarbamoyl}-2-phenylethylcarbamoyl)-4-(benzyloxycarbonylamino)butyric acid benzyl ester (872983-57-8)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1016/j.bmc.2005.08.019

Reference yield:

3-amino-3-propyldihydrofuran-2-one (872983-41-0) → (4S)-4-((1S)-1-{1-benzylcarbamoyl-1-[2-(tert-butyldiphenylsiloxy)ethyl]butylcarbamoyl}-2-phenylethylcarbamoyl)-4-(benzyloxycarbonylamino)butyric acid benzyl ester (872983-57-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.8 g / 2-phenylbenzoxazole; ethyldiisopropylamine / CH₂Cl₂ / 0 °C

2: 1.8 g / lithium hydroxide / tetrahydrofuran; H₂O / 0 °C

3: 1.66 g / imidazole / CH₂Cl₂ / 0 °C

4: 1.5 g / 1-hydroxy-1H-benzotriazole; 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide HCl; triethylamine / CH₂Cl₂ / 0 °C

5: 100 percent / H₂ / Pd-C / methanol / 20 °C

6: 98 percent / 1-hydroxy-1H-benzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; triethylamine / CH₂Cl₂ / 0 °C

With 1H-imidazole; lithium hydroxide; 2-phenylbenzo[d]oxazole; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/j.bmc.2005.08.019

Reference yield:

2-amino-2-(2-hydroxy-ethyl)-pentanoic acid → (4S)-4-((1S)-1-{1-benzylcarbamoyl-1-[2-(tert-butyldiphenylsiloxy)ethyl]butylcarbamoyl}-2-phenylethylcarbamoyl)-4-(benzyloxycarbonylamino)butyric acid benzyl ester (872983-57-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 2.4 g / hydrochloric acid / 16 h / Heating

2: 1.8 g / 2-phenylbenzoxazole; ethyldiisopropylamine / CH₂Cl₂ / 0 °C

3: 1.8 g / lithium hydroxide / tetrahydrofuran; H₂O / 0 °C

4: 1.66 g / imidazole / CH₂Cl₂ / 0 °C

5: 1.5 g / 1-hydroxy-1H-benzotriazole; 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide HCl; triethylamine / CH₂Cl₂ / 0 °C

6: 100 percent / H₂ / Pd-C / methanol / 20 °C

7: 98 percent / 1-hydroxy-1H-benzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; triethylamine / CH₂Cl₂ / 0 °C

With 1H-imidazole; hydrogenchloride; lithium hydroxide; 2-phenylbenzo[d]oxazole; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/j.bmc.2005.08.019

upstream raw materials:

2-(2-amino-3-phenyl-propionylamino)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-pentanoic acid benzylamide

N-benzyloxycarbonyl-5-O-benzyl-L-glutamic acid

3-amino-3-propyldihydrofuran-2-one

2-amino-2-(2-hydroxy-ethyl)-pent-4-enoic acid

Downstream raw materials:

(S)-4-{(S)-1-[1-Benzylcarbamoyl-1-(2-hydroxy-ethyl)-butylcarbamoyl]-2-phenyl-ethylcarbamoyl}-4-benzyloxycarbonylamino-butyric acid benzyl ester

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