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

Base Information

• Chemical Name: benzyl (2S,4S)-4-(tert-butoxycarbonyl)amino-5-(2-methoxyethoxy)methoxy-2-methylpentanoate
• CAS No.: 911050-95-8
• Molecular Formula: C₂₂H₃₅NO₇
• Molecular Weight: 425.522
• Mol file: 911050-95-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about benzyl (2S,4S)-4-(tert-butoxycarbonyl)amino-5-(2-methoxyethoxy)methoxy-2-methylpentanoate 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:

benzyl (4S)-4-(tert-butoxycarbonyl)amino-5-[(2-methoxyethoxy)methoxy]pentanoate (299432-52-3) + methyl iodide (74-88-4) → benzyl (2S,4S)-4-(tert-butoxycarbonyl)amino-5-(2-methoxyethoxy)methoxy-2-methylpentanoate (911050-95-8)

Guidance literature:

benzyl (4S)-4-(tert-butoxycarbonyl)amino-5-[(2-methoxyethoxy)methoxy]pentanoate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 3h;

DOI:10.1016/j.bmc.2006.05.040

Reference yield:

benzyl (S)-4-(t-butyloxycarbonylamino)-5-hydroxypentanoate (79069-62-8) → benzyl (2S,4S)-4-(tert-butoxycarbonyl)amino-5-(2-methoxyethoxy)methoxy-2-methylpentanoate (911050-95-8)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1016/j.bmc.2006.05.040

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

upstream raw materials:

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

methyl iodide

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

Downstream raw materials:

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

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