(4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone

Base Information

• Chemical Name: (4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone
• CAS No.: 136620-81-0
• Molecular Formula: C₁₉H₁₈N₄O₄
• Molecular Weight: 366.376
• Mol file: 136620-81-0.mol

Synonyms:(4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone

Chemical Property of (4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone

There total 2 articles about (4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-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: 80.0%

(4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone (136620-80-9) → (4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone (136620-81-0)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; for 5h; Ambient temperature;

DOI:10.1021/jo00038a048

Reference yield:

(4R)-3-(bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone (110905-24-3) → (4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone (136620-81-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) Bu₂OTf, NEt₃

2: 80 percent / NaN₃ / dimethylsulfoxide / 5 h / Ambient temperature

With sodium azide; triethylamine; In dimethyl sulfoxide;

DOI:10.1021/jo00038a048

Reference yield: 88.0%

aqueous sodium bisulfate + Cl2 CH2 + (4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone (136620-81-0) → (2S,3S)-2-azido-3-phenyl-3-hydroxypropionic acid methyl ester (133179-94-9)

Guidance literature:

With methylmagnesium bromide; In methanol; diethyl ether;

upstream raw materials:

(4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone

(4R)-3-(bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone

Downstream raw materials:

(2S,3S)-2-azido-3-phenyl-3-hydroxypropionic acid methyl ester

(4S,5R)-2-Oxo-5-phenyl-oxazolidine-4-carboxylic acid methyl ester

(2R,3R)-2-((tert-butyloxycarbonyl)amino)-3-((4-methylbenzyl)thio)-3-phenylpropionic acid

erythro-N-(tert-butoxycarbonyl)-β-hydroxy-L-phenylalanine methyl ester