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

Base Information

• Chemical Name: benzyl (2S,4S)-4-(tert-butoxycarbonyl)amino-5-(2,2-dimethylpropanoyl)oxy-2-ethylpentanoate
• CAS No.: 911050-54-9
• Molecular Formula: C₂₄H₃₇NO₆
• Molecular Weight: 435.561
• Mol file: 911050-54-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about benzyl (2S,4S)-4-(tert-butoxycarbonyl)amino-5-(2,2-dimethylpropanoyl)oxy-2-ethylpentanoate 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: 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:

pivaloyl chloride (3282-30-2) → benzyl (2S,4S)-4-(tert-butoxycarbonyl)amino-5-(2,2-dimethylpropanoyl)oxy-2-ethylpentanoate (911050-54-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 72 percent / pyridine / 1 h / 20 °C

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

2.2: 55 percent / tetrahydrofuran / 3 h / -78 °C

With pyridine; lithium hexamethyldisilazane; In tetrahydrofuran;

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-(2,2-dimethylpropanoyl)oxy-2-ethylpentanoate (911050-54-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 72 percent / pyridine / 1 h / 20 °C

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

2.2: 55 percent / tetrahydrofuran / 3 h / -78 °C

With pyridine; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1016/j.bmc.2006.05.040

upstream raw materials:

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

ethyl iodide

pivaloyl chloride

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

Downstream raw materials:

benzyl (2S,4S)-5-(2,2-dimethylpropanoyl)oxy-2-ethyl-4-[(4-phenoxybenzoyl)amino]pentanoate

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