(2R,3R)-2-((tert-butyloxycarbonyl)amino)-3-((4-methylbenzyl)thio)-3-phenylpropionic acid

Base Information

• Chemical Name: (2R,3R)-2-((tert-butyloxycarbonyl)amino)-3-((4-methylbenzyl)thio)-3-phenylpropionic acid
• CAS No.: 136620-85-4
• Molecular Formula: C₂₂H₂₇NO₄S
• Molecular Weight: 401.527
• Mol file: 136620-85-4.mol

Synonyms:(2R,3R)-2-((tert-butyloxycarbonyl)amino)-3-((4-methylbenzyl)thio)-3-phenylpropionic acid

Chemical Property of (2R,3R)-2-((tert-butyloxycarbonyl)amino)-3-((4-methylbenzyl)thio)-3-phenylpropionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2-((tert-butyloxycarbonyl)amino)-3-((4-methylbenzyl)thio)-3-phenylpropionic acid

There total 9 articles about (2R,3R)-2-((tert-butyloxycarbonyl)amino)-3-((4-methylbenzyl)thio)-3-phenylpropionic acid 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: 77.0%

methyl (2R,3R)-2-((tert-butyloxycarbonyl)amino)-3-((4-methylbenzyl)thio)-3-phenylpropionic acid (136620-84-3) → (2R,3R)-2-((tert-butyloxycarbonyl)amino)-3-((4-methylbenzyl)thio)-3-phenylpropionic acid (136620-85-4)

Guidance literature:

With lithium chloride; In N,N-dimethyl-formamide; at 90 ℃; for 96h;

DOI:10.1021/jo00038a048

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2R,3R)-2-((tert-butyloxycarbonyl)amino)-3-((4-methylbenzyl)thio)-3-phenylpropionic acid (136620-85-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / H₂ / 10percent Pd-C / ethyl acetate / 2 h / Ambient temperature

2: NEt₃ / CH₂Cl₂ / 0.33 h / 0 °C

3: 69 percent / dimethylformamide / 20 h / Ambient temperature

4: 79 percent / aq. NaOH / methanol / 0.33 h

5: 77 percent / LiCl / dimethylformamide / 96 h / 90 °C

With sodium hydroxide; hydrogen; triethylamine; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00038a048

Reference yield:

(2S,3S)-2-azido-3-phenyl-3-hydroxypropionic acid methyl ester (133179-94-9) → (2R,3R)-2-((tert-butyloxycarbonyl)amino)-3-((4-methylbenzyl)thio)-3-phenylpropionic acid (136620-85-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / H₂ / 10percent Pd-C / ethyl acetate / 2 h / Ambient temperature

2: NEt₃ / CH₂Cl₂ / 0.33 h / 0 °C

3: 69 percent / dimethylformamide / 20 h / Ambient temperature

4: 79 percent / aq. NaOH / methanol / 0.33 h

5: 77 percent / LiCl / dimethylformamide / 96 h / 90 °C

With sodium hydroxide; hydrogen; triethylamine; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00038a048

upstream raw materials:

methyl (2R,3R)-2-((tert-butyloxycarbonyl)amino)-3-((4-methylbenzyl)thio)-3-phenylpropionic acid

di-tert-butyl dicarbonate

(2S,3S)-2-azido-3-phenyl-3-hydroxypropionic acid methyl ester

benzaldehyde