159406-31-2

Basic information

• Product Name: (4S,5R)-5-Methyl-4-phenyl-2-oxazolidinone
• Synonyms: (4S,5R)-5-Methyl-4-phenyl-2-oxazolidinone
• CAS NO: 159406-31-2
• Molecular Weight: 177.203
• Mol File: 159406-31-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (4S,5R)-5-Methyl-4-phenyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R)-5-Methyl-4-phenyl-2-oxazolidinone(159406-31-2)
• EPA Substance Registry System: (4S,5R)-5-Methyl-4-phenyl-2-oxazolidinone(159406-31-2)

Safety Data

• Hazardous Substances Data: 159406-31-2(Hazardous Substances Data)

Upstream product

• 88082-67-1 (1S,2R)-1-amino-1-phenylpropan-2-ol 
• 526217-24-3 tert-butyl (1S,2R)-2-hydroxy-1-phenylpropylcarbamate 
• 14212-54-5 (+)-(R,R)-β-methylstyrene oxide 
• 591-51-5 phenyllithium 
• 205437-22-5 (4RS,5R)-4-methoxy-5-methyl-1,3-oxazolidin-2-one 

Downstream Products

• 863709-49-3 (4S,5R)-3-((E)-hex-1-enyl)-5-methyl-4-phenyloxazolidin-2-one 
• 1453081-87-2 (4S,5R)-3-(2-bromo-2-methylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one 

Relevant articles and documents

Diastereoselective Amidoalkylation Reactions of Electrochemically Methoxylated Chiral 2-Oxazolidinones with Organocopper Reagents

(4RS,5R)-4-Methoxy-5-methyl-2-oxazolidinone (2ab), easily obtained by electrochemical decarboxylative methoxylation of the cyclic L-threonine derivative (4S,5R)-5-methyl-2-oxazolidinone-4-carboxylic acid (1), acts as effective diastereoselective amidoalkylation reagent.The methoxy group exchange in 2ab can be performed with higher order organocuprates (R3Cu2Li) in the presence of BF3*OEt2.The 4-alkyl- or 4-aryl-substituted 2-oxazolidinones 3-6 can be obtained with trans diastereoselectivities between 75 and 98percent in SN1 fashion via the intermediate N-acylimine.On the contrary, the N-methylated (4RS,5R)-4-methoxy-3,5-dimethyl-2-oxazolidinone (7ab) undergoes methoxy group exchange under identical conditions mainly via the SN2 mechanism.Thus, starting from trans-7a mainly cis-8b is formed with 76percent ds.The described procedures make cis- or trans-4-alkyl-5-methyl-2-oxazolidinones and the respective dichiral 2-amino alcohols selectively available by a short reaction sequence.

Examining the origin of selectivity in the reaction of racemic alcohols with chiral N-phosphoryl oxazolidinones

A range of known and novel N-phosphoryl oxazolidinones and imidazolidinones were prepared and screened in the kinetic resolution of a range of racemic magnesium chloroalkoxides. Models are proposed to account for the enantioselectivity achieved based on a combination of chiral relay effects, generation of transient stereochemistry and the structure of the intermediate magnesium alkoxide.