1-<(2R,3S)-3-(N²-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl>-N-tert-butyl-L-prolinamide

Base Information

• Chemical Name: 1-<(2R,3S)-3-(N²-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl>-N-tert-butyl-L-prolinamide
• CAS No.: 139758-12-6
• Molecular Formula: C₃₁H₄₁N₅O₇
• Molecular Weight: 595.696

Synonyms:1-<(2R,3S)-3-(N²-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl>-N-tert-butyl-L-prolinamide

Chemical Property of 1-<(2R,3S)-3-(N²-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl>-N-tert-butyl-L-prolinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-<(2R,3S)-3-(N²-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl>-N-tert-butyl-L-prolinamide

There total 6 articles about 1-<(2R,3S)-3-(N²-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl>-N-tert-butyl-L-prolinamide 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: 51.0%

N-benzyloxycarbonyl-L-asparagine p-nitrophenyl ester (3256-57-3) + 1-<(2R,3S)-3-amino-2-hydroxy-4-phenylbutyryl>-N-tert-butyl-L-prolinamide (165522-26-9) → 1-<(2R,3S)-3-(N2-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl>-N-tert-butyl-L-prolinamide (139758-12-6)

Guidance literature:

In N,N-dimethyl-formamide; a) 0 deg C, 1 h, b) RT, 4 h;

DOI:10.1248/cpb.42.2636

Reference yield:

(1S)-2-(tert-butylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester (68030-64-8) → 1-<(2R,3S)-3-(N2-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl>-N-tert-butyl-L-prolinamide (139758-12-6)

Guidance literature:

Multi-step reaction with 4 steps

1: HCl / dioxane; CH₂Cl₂ / 2 h

2: 1-hydroxybenzotriazol; N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide*HCl; TEA / dimethylformamide

3: HCl / dioxane; CH₂Cl₂ / 2 h

4: 40 percent / 1-hydroxybenzotriazol; TEA / dimethylformamide

With hydrogenchloride; TEA; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.48.1310

Reference yield:

[(1S,2R)-1-Benzyl-3-((S)-2-tert-butylcarbamoyl-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester (143935-61-9) → 1-<(2R,3S)-3-(N2-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl>-N-tert-butyl-L-prolinamide (139758-12-6)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / dioxane; CH₂Cl₂ / 2 h

2: 40 percent / 1-hydroxybenzotriazol; TEA / dimethylformamide

With hydrogenchloride; TEA; benzotriazol-1-ol; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.48.1310

upstream raw materials:

N-benzyloxycarbonyl-L-asparagine p-nitrophenyl ester

1-<(2R,3S)-3-amino-2-hydroxy-4-phenylbutyryl>-N-tert-butyl-L-prolinamide

1-(tert-butoxycarbonyl)-L-proline

(1S)-2-(tert-butylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

1-<(3S)-3-(N²-benzyloxycarbonyl-L-asparaginyl)amino-2-oxo-4-phenylbutyryl>-N-tert-butyl-L-prolinamide

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