{(S)-1-[(1S,2R)-1-Benzyl-3-(1-benzyl-3-tert-butyl-ureido)-2-hydroxy-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester

Base Information

• Chemical Name: {(S)-1-[(1S,2R)-1-Benzyl-3-(1-benzyl-3-tert-butyl-ureido)-2-hydroxy-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester
• CAS No.: 143224-85-5
• Molecular Formula: C₃₄H₄₃N₅O₆
• Molecular Weight: 617.745

Synonyms:{(S)-1-[(1S,2R)-1-Benzyl-3-(1-benzyl-3-tert-butyl-ureido)-2-hydroxy-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester

Chemical Property of {(S)-1-[(1S,2R)-1-Benzyl-3-(1-benzyl-3-tert-butyl-ureido)-2-hydroxy-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester

Chemical Property:

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Technology Process of {(S)-1-[(1S,2R)-1-Benzyl-3-(1-benzyl-3-tert-butyl-ureido)-2-hydroxy-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester

There total 7 articles about {(S)-1-[(1S,2R)-1-Benzyl-3-(1-benzyl-3-tert-butyl-ureido)-2-hydroxy-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic 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:

N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane (128018-44-0) → {(S)-1-[(1S,2R)-1-Benzyl-3-(1-benzyl-3-tert-butyl-ureido)-2-hydroxy-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester (143224-85-5)

Guidance literature:

Multi-step reaction with 4 steps

1: propan-2-ol / Heating

2: CH₂Cl₂ / Ambient temperature

3: H₂ / Pd(C) / ethanol

4: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC), 1-hydroxybenzotriazole hydrate (HOBT) / dimethylformamide

With hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm00054a014

Reference yield:

(S)-benzyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate (26049-94-5) → {(S)-1-[(1S,2R)-1-Benzyl-3-(1-benzyl-3-tert-butyl-ureido)-2-hydroxy-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester (143224-85-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 43 percent / NaBH₄ / methanol; tetrahydrofuran

2: 90 percent / KOH / ethanol

3: propan-2-ol / Heating

4: CH₂Cl₂ / Ambient temperature

5: H₂ / Pd(C) / ethanol

6: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC), 1-hydroxybenzotriazole hydrate (HOBT) / dimethylformamide

With potassium hydroxide; sodium tetrahydroborate; hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm00054a014

Reference yield:

N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol (128018-43-9) → {(S)-1-[(1S,2R)-1-Benzyl-3-(1-benzyl-3-tert-butyl-ureido)-2-hydroxy-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester (143224-85-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / KOH / ethanol

2: propan-2-ol / Heating

3: CH₂Cl₂ / Ambient temperature

4: H₂ / Pd(C) / ethanol

5: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC), 1-hydroxybenzotriazole hydrate (HOBT) / dimethylformamide

With potassium hydroxide; hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm00054a014

upstream raw materials:

N-benzyloxycarbonyl-L-asparagine

1-((2R,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-1-benzyl-3-tert-butyl-urea

N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane

(S)-benzyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate

Downstream raw materials:

(S)-2-Amino-N¹-[(1S,2R)-1-benzyl-3-(1-benzyl-3-tert-butyl-ureido)-2-hydroxy-propyl]-succinamide

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