(2S,3R)-3-hydroxy-2-(((tert-butyloxy)carbonyl)amino)-4-((phenylmethoxy)phenyl)butanoic acid

Base Information

• Chemical Name: (2S,3R)-3-hydroxy-2-(((tert-butyloxy)carbonyl)amino)-4-((phenylmethoxy)phenyl)butanoic acid
• CAS No.: 110905-22-1
• Molecular Formula: C₂₂H₂₇NO₆
• Molecular Weight: 401.459
• Mol file: 110905-22-1.mol

Synonyms:(2S,3R)-3-hydroxy-2-(((tert-butyloxy)carbonyl)amino)-4-((phenylmethoxy)phenyl)butanoic acid

Chemical Property of (2S,3R)-3-hydroxy-2-(((tert-butyloxy)carbonyl)amino)-4-((phenylmethoxy)phenyl)butanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-hydroxy-2-(((tert-butyloxy)carbonyl)amino)-4-((phenylmethoxy)phenyl)butanoic acid

There total 1 articles about (2S,3R)-3-hydroxy-2-(((tert-butyloxy)carbonyl)amino)-4-((phenylmethoxy)phenyl)butanoic 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: 83.0%

methyl (4S,5R)-3-((tert-butyloxy)carbonyl)-5-((4'-(phenylmethoxy)phenyl)methyl)-2-oxazolidine-4-carboxylate (110905-21-0) → (4S,5R)-5-(4-Benzyloxy-benzyl)-2-oxo-oxazolidine-4-carboxylic acid + (2S,3R)-3-hydroxy-2-(((tert-butyloxy)carbonyl)amino)-4-((phenylmethoxy)phenyl)butanoic acid (110905-22-1)

Guidance literature:

With lithium hydroxide; In 1,4-dioxane; water; Ambient temperature;

DOI:10.1021/ja00257a041

Reference yield:

(2S,3R)-3-hydroxy-2-(((tert-butyloxy)carbonyl)amino)-4-((phenylmethoxy)phenyl)butanoic acid (110905-22-1) → (2S,3S,4S)-1-{(2S,3R)-2-[(2S,3R)-2-Amino-3-hydroxy-4-(4-hydroxy-phenyl)-butyrylamino]-3-hydroxy-butyryl}-3-hydroxy-4-methyl-pyrrolidine-2-carboxylic acid methyl ester; compound with trifluoro-acetic acid

Guidance literature:

Multi-step reaction with 2 steps

1: N-methylmorpholine, hydroxybenzotriazole monohydrate, 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 0 deg C, 2 h, room temperature, 20 h

2: 1.) H₂, 2.) trifluoroacetic acid / 1.) 10percent Pd/C / 1.) ethanol, acetic acid, 5 h, 2.) 0 deg C, 30 min

With 4-methyl-morpholine; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1021/ja00257a041

Reference yield:

(2S,3S,4S)-1-((2S,3R)-2-Amino-3-hydroxy-butyryl)-3-hydroxy-4-methyl-pyrrolidine-2-carboxylic acid methyl ester + (2S,3R)-3-hydroxy-2-(((tert-butyloxy)carbonyl)amino)-4-((phenylmethoxy)phenyl)butanoic acid (110905-22-1) → (2S,3S,4S)-1-{(2S,3R)-2-[(2S,3R)-4-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino]-3-hydroxy-butyryl}-3-hydroxy-4-methyl-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; Yield given; 0 deg C, 2 h, room temperature, 20 h;

DOI:10.1021/ja00257a041

upstream raw materials:

methyl (4S,5R)-3-((tert-butyloxy)carbonyl)-5-((4'-(phenylmethoxy)phenyl)methyl)-2-oxazolidine-4-carboxylate