(2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-(2-azidoethyl)-4-benzyloxazolidinone

Base Information

• Chemical Name: (2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-(2-azidoethyl)-4-benzyloxazolidinone
• CAS No.: 159801-68-0
• Molecular Formula: C₂₆H₂₄N₄O₄
• Molecular Weight: 456.501
• Mol file: 159801-68-0.mol

Synonyms:(2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-(2-azidoethyl)-4-benzyloxazolidinone

Chemical Property of (2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-(2-azidoethyl)-4-benzyloxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-(2-azidoethyl)-4-benzyloxazolidinone

There total 3 articles about (2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-(2-azidoethyl)-4-benzyloxazolidinone 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: 93.0%

(2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-benzyl-4-<2-(methylsulfonyloxy)ethyl>oxazolidinone (159801-67-9) → (2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-(2-azidoethyl)-4-benzyloxazolidinone (159801-68-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 40 ℃; for 20h;

DOI:10.1021/jo00104a022

Reference yield:

(2S,4S)-benzyl 4-benzyl-5-oxo-2-phenyloxazolidine-3-carboxylate (95260-60-9) → (2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-(2-azidoethyl)-4-benzyloxazolidinone (159801-68-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) KN(TMS)2, 2.) BF₃*Et₂O / 1.) THF, -78 deg C, 15 min, 2.) -78 deg C, 1.5 h

2: 88 percent / pyridine / CH₂Cl₂ / 48 h / 20 °C

3: 93 percent / NaN₃ / dimethylformamide / 20 h / 40 °C

With pyridine; sodium azide; boron trifluoride diethyl etherate; potassium hexamethylsilazane; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00104a022

Reference yield:

(2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-benzyl-4-(2-hydroxyethyl)oxazolidinone (159801-66-8) → (2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-(2-azidoethyl)-4-benzyloxazolidinone (159801-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / pyridine / CH₂Cl₂ / 48 h / 20 °C

2: 93 percent / NaN₃ / dimethylformamide / 20 h / 40 °C

With pyridine; sodium azide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00104a022

upstream raw materials:

(2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-benzyl-4-<2-(methylsulfonyloxy)ethyl>oxazolidinone

(2S,4S)-benzyl 4-benzyl-5-oxo-2-phenyloxazolidine-3-carboxylate

(2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-benzyl-4-(2-hydroxyethyl)oxazolidinone

Downstream raw materials:

(2'R)-2-<<<2'-Benzyl-2',4'-bis<(benzyloxycarbonyl)amino>-1'-oxobutyl>amino>methyl>-1,3-dithiane

[(R)-3-Benzyloxycarbonylamino-3-(2,2-dimethoxy-ethylcarbamoyl)-4-phenyl-butyl]-carbamic acid benzyl ester

(2R)-2-Benzyl-2,4-bis<(benzyloxycarbonyl)amino>butyric acid

(4R,1'S)-2-<1'-<(benzyloxycarbonyl)-amino>ethyl>-4-benzyl-4-<<(2,2-dimethoxyethyl)amino>carbonyl>-3,4,5,6-tetrahydropyrimidine