methyl ((2S,3R)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutanoyl)-L-leucinate

Base Information

• Chemical Name: methyl ((2S,3R)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutanoyl)-L-leucinate
• CAS No.: 77119-86-9
• Molecular Formula: C₂₂H₃₄N₂O₆
• Molecular Weight: 422.522
• Mol file: 77119-86-9.mol

Synonyms:methyl ((2S,3R)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutanoyl)-L-leucinate

Chemical Property of methyl ((2S,3R)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutanoyl)-L-leucinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl ((2S,3R)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutanoyl)-L-leucinate

There total 4 articles about methyl ((2S,3R)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutanoyl)-L-leucinate 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: 62.0%

methyl (L)-leucinate hydrochloride (7517-19-3) + (2S,3R)-3-[(tert-butoxycarbonyl) amino]-2-hydroxy-4-phenyl-butanoic acid (62023-65-8) → methyl ((2S,3R)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutanoyl)-L-leucinate (77119-86-9)

Guidance literature:

(2S,3R)-3-[(tert-butoxycarbonyl) amino]-2-hydroxy-4-phenyl-butanoic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 0.5h;

methyl (L)-leucinate hydrochloride; With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1016/j.bioorg.2021.105343

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + methyl (2S)-2-(((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl)amino)-4-methylpentanoate (65322-89-6) → methyl ((2S,3R)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutanoyl)-L-leucinate (77119-86-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 2.5h;

DOI:10.1016/j.bmcl.2008.04.031

Reference yield:

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid (59554-14-2) → methyl ((2S,3R)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutanoyl)-L-leucinate (77119-86-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.5 h / 0 °C

2.2: 0 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In dichloromethane;

DOI:10.1016/j.bioorg.2021.105343

upstream raw materials:

di-tert-butyl dicarbonate

methyl (2S)-2-(((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl)amino)-4-methylpentanoate

methyl (L)-leucinate hydrochloride

(2S,3R)-3-[(tert-butoxycarbonyl) amino]-2-hydroxy-4-phenyl-butanoic acid

Downstream raw materials:

(2S)-2-[[(2S,3R)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoic acid

Refernces

• 1、 Sato, Shinichi,Aoyama, Hiroshi,Miyachi, Hiroyuki,Naito, Mikihiko,Hashimoto, Yuichi. "Demonstration of direct binding of cIAP1 degradation-promoting bestatin analogs to BIR3 domain: Synthesis and application of fluorescent bestatin ester analogs". scheme or table. p. 3354 - 3358. Retrieved 2009/04/05.