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

Base Information

• Chemical Name: methyl (4S,5R)-3-((tert-butyloxy)carbonyl)-5-((4'-(phenylmethoxy)phenyl)methyl)-2-oxazolidine-4-carboxylate
• CAS No.: 110905-21-0
• Molecular Formula: C₂₄H₂₇NO₇
• Molecular Weight: 441.481
• Mol file: 110905-21-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about methyl (4S,5R)-3-((tert-butyloxy)carbonyl)-5-((4'-(phenylmethoxy)phenyl)methyl)-2-oxazolidine-4-carboxylate 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:

2,2-dimethylpropanoic anhydride (1538-75-6) + methyl (4S,5R)-5-((4'-(phenylmethoxy)phenyl)methyl)-2-thioxooxazolidine-4-carboxylate → methyl (4S,5R)-3-((tert-butyloxy)carbonyl)-5-((4'-(phenylmethoxy)phenyl)methyl)-2-oxazolidine-4-carboxylate (110905-21-0)

Guidance literature:

With dmap; formic acid; dihydrogen peroxide; Yield given. Multistep reaction; 1.) methylen chloride, 30 min, 2.) water, 30 min;

DOI:10.1021/ja00257a041

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:

methyl (4S,5R)-3-((tert-butyloxy)carbonyl)-5-((4'-(phenylmethoxy)phenyl)methyl)-2-oxazolidine-4-carboxylate (110905-21-0) → (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 3 steps

1: 83 percent / lithium hydroxide / dioxane; H₂O / Ambient temperature

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

3: 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; lithium hydroxide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00257a041

upstream raw materials:

2,2-dimethylpropanoic anhydride

Downstream raw materials:

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