benzyl (4S)-4-(tert-butoxycarbonyl)amino-5-[(2,2-dimethylpropanoyl)oxy]pentanoate

Base Information

• Chemical Name: benzyl (4S)-4-(tert-butoxycarbonyl)amino-5-[(2,2-dimethylpropanoyl)oxy]pentanoate
• CAS No.: 911050-94-7
• Molecular Formula: C₂₂H₃₃NO₆
• Molecular Weight: 407.507
• Mol file: 911050-94-7.mol

Synonyms:benzyl (4S)-4-(tert-butoxycarbonyl)amino-5-[(2,2-dimethylpropanoyl)oxy]pentanoate

Chemical Property of benzyl (4S)-4-(tert-butoxycarbonyl)amino-5-[(2,2-dimethylpropanoyl)oxy]pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (4S)-4-(tert-butoxycarbonyl)amino-5-[(2,2-dimethylpropanoyl)oxy]pentanoate

There total 1 articles about benzyl (4S)-4-(tert-butoxycarbonyl)amino-5-[(2,2-dimethylpropanoyl)oxy]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: 72.0%

pivaloyl chloride (3282-30-2) + benzyl (S)-4-(t-butyloxycarbonylamino)-5-hydroxypentanoate (79069-62-8) → benzyl (4S)-4-(tert-butoxycarbonyl)amino-5-[(2,2-dimethylpropanoyl)oxy]pentanoate (911050-94-7)

Guidance literature:

With pyridine; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2006.05.040

Reference yield: 55.0%

benzyl (4S)-4-(tert-butoxycarbonyl)amino-5-[(2,2-dimethylpropanoyl)oxy]pentanoate (911050-94-7) + ethyl iodide (75-03-6) → benzyl (2S,4S)-4-(tert-butoxycarbonyl)amino-5-(2,2-dimethylpropanoyl)oxy-2-ethylpentanoate (911050-54-9)

Guidance literature:

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

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

DOI:10.1016/j.bmc.2006.05.040

Reference yield:

benzyl (4S)-4-(tert-butoxycarbonyl)amino-5-[(2,2-dimethylpropanoyl)oxy]pentanoate (911050-94-7) → (2S,4S)-5-(2,2-dimethylpropanoyl)oxy-2-methyl-4-[(4-phenoxybenzoyl)amino]pentanoic acid (911050-99-2)

Guidance literature:

Multi-step reaction with 3 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: 84 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; 1-hydroxybenzotriazole monohydrate; triethylamine / dimethylformamide / 0 °C

3.1: 86 percent / hydrogen / Pd/C / methanol / 0.67 h

With hydrogen; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/j.bmc.2006.05.040

upstream raw materials:

pivaloyl chloride

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

Downstream raw materials:

benzyl (2S,4S)-4-(tert-butoxycarbonyl)amino-5-(2,2-dimethylpropanoyl)oxy-2-ethylpentanoate

benzyl (2S,4S)-4-(tert-butoxycarbonyl)amino-5-(2,2-dimethylpropanoyl)oxy-2-methylpentanoate

(2S,4S)-5-(2,2-dimethylpropanoyl)oxy-2-methyl-4-[(4-phenoxybenzoyl)amino]pentanoic acid

(2S,4S)-5-(2,2-dimethylpropanoyl)oxy-2-ethyl-4-[(4-phenoxybenzoyl)amino]pentanoic acid