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

Base Information

• Chemical Name: (2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-benzyl-4-<2-(methylsulfonyloxy)ethyl>oxazolidinone
• CAS No.: 159801-67-9
• Molecular Formula: C₂₇H₂₇NO₇S
• Molecular Weight: 509.58
• Mol file: 159801-67-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-benzyl-4-<2-(methylsulfonyloxy)ethyl>oxazolidinone 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: 88.0%

methanesulfonyl chloride (124-63-0) + (2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-benzyl-4-(2-hydroxyethyl)oxazolidinone (159801-66-8) → (2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-benzyl-4-<2-(methylsulfonyloxy)ethyl>oxazolidinone (159801-67-9)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 48h;

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-benzyl-4-<2-(methylsulfonyloxy)ethyl>oxazolidinone (159801-67-9)

Guidance literature:

Multi-step reaction with 2 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

With pyridine; boron trifluoride diethyl etherate; potassium hexamethylsilazane; In dichloromethane;

DOI:10.1021/jo00104a022

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

upstream raw materials:

methanesulfonyl chloride

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

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

Downstream raw materials:

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

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

(4R,1'S)-2-<1'-<(Benzyloxycarbonyl)-amino>ethyl>-4-benzyl-4-carboxy-3,4,5,6-tetrahydropyrimidine

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