benzyl (2S,4S)-5-(2-methoxyethoxy)methoxy-2-methyl-4-[(4-phenoxybenzoyl)amino]pentanoate

Base Information

• Chemical Name: benzyl (2S,4S)-5-(2-methoxyethoxy)methoxy-2-methyl-4-[(4-phenoxybenzoyl)amino]pentanoate
• CAS No.: 911050-97-0
• Molecular Formula: C₃₀H₃₅NO₇
• Molecular Weight: 521.61
• Mol file: 911050-97-0.mol

Synonyms:benzyl (2S,4S)-5-(2-methoxyethoxy)methoxy-2-methyl-4-[(4-phenoxybenzoyl)amino]pentanoate

Chemical Property of benzyl (2S,4S)-5-(2-methoxyethoxy)methoxy-2-methyl-4-[(4-phenoxybenzoyl)amino]pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S,4S)-5-(2-methoxyethoxy)methoxy-2-methyl-4-[(4-phenoxybenzoyl)amino]pentanoate

There total 3 articles about benzyl (2S,4S)-5-(2-methoxyethoxy)methoxy-2-methyl-4-[(4-phenoxybenzoyl)amino]pentanoate 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: 85.0%

benzyl (2S,4S)-4-(tert-butoxycarbonyl)amino-5-(2-methoxyethoxy)methoxy-2-methylpentanoate (911050-95-8) + 4-Phenoxybenzoic acid (2215-77-2) → benzyl (2S,4S)-5-(2-methoxyethoxy)methoxy-2-methyl-4-[(4-phenoxybenzoyl)amino]pentanoate (911050-97-0)

Guidance literature:

benzyl (2S,4S)-4-(tert-butoxycarbonyl)amino-5-(2-methoxyethoxy)methoxy-2-methylpentanoate; With trifluoroacetic acid; In dichloromethane; water; at 0 ℃; for 0.5h;

4-Phenoxybenzoic acid; With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1016/j.bmc.2006.05.040

Reference yield:

benzyl (4S)-4-(tert-butoxycarbonyl)amino-5-[(2-methoxyethoxy)methoxy]pentanoate (299432-52-3) → benzyl (2S,4S)-5-(2-methoxyethoxy)methoxy-2-methyl-4-[(4-phenoxybenzoyl)amino]pentanoate (911050-97-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

1.2: tetrahydrofuran / 3 h / -78 °C

2.1: trifluoroacetic acid / CH₂Cl₂; H₂O / 0.5 h / 0 °C

2.2: 85 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; 1-hydroxybenzotriazole monohydrate; triethylamine / dimethylformamide / 0 °C

With trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.bmc.2006.05.040

Reference yield:

benzyl (S)-4-(t-butyloxycarbonylamino)-5-hydroxypentanoate (79069-62-8) → benzyl (2S,4S)-5-(2-methoxyethoxy)methoxy-2-methyl-4-[(4-phenoxybenzoyl)amino]pentanoate (911050-97-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / ethyldiisopropylamine / CH₂Cl₂ / 2 h / 20 °C

2.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

2.2: tetrahydrofuran / 3 h / -78 °C

3.1: trifluoroacetic acid / CH₂Cl₂; H₂O / 0.5 h / 0 °C

3.2: 85 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; 1-hydroxybenzotriazole monohydrate; triethylamine / dimethylformamide / 0 °C

With N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.bmc.2006.05.040

upstream raw materials:

benzyl (2S,4S)-4-(tert-butoxycarbonyl)amino-5-(2-methoxyethoxy)methoxy-2-methylpentanoate

4-Phenoxybenzoic acid

benzyl (4S)-4-(tert-butoxycarbonyl)amino-5-[(2-methoxyethoxy)methoxy]pentanoate

benzyl (S)-4-(t-butyloxycarbonylamino)-5-hydroxypentanoate

Downstream raw materials:

(2S,4S)-5-(2-methoxyethoxy)methoxy-2-methyl-4-[(4-phenoxybenzoyl)amino]pentanoic acid