(4S,5R)-(-)-4-Methyl-5-phenyl-2-oxazolidinone Chiral Auxiliary CAS 16251-45-9 lab use

(4S,5R)-(-)-4-Methyl-5-phenyl-2-oxazolidinone (CAS 16251-45-9) is a chiral oxazolidinone derivative widely employed as a chiral auxiliary in asymmetric synthesis . This compound features a five-membered oxazolidinone ring with a methyl group at the 4-position and a phenyl group at the 5-position, with the (4S,5R) configuration enabling high stereoselectivity in the formation of chiral centers in target molecules . It is also known by synonyms including (4S,5R)-4-Methyl-5-phenyloxazolidin-2-one and (4S,5R)-(-)-4-Methyl-2-oxo-5-phenyl-1,3-oxazolidine .

Chemical Characteristics:

• Contains a chiral oxazolidinone ring system with defined (4S,5R) stereochemistry

• Molecular weight: 177.20 g/mol 

• Melting point: 121-123°C 

• Optical rotation: -168° (c = 2 in chloroform) 

• Density: 1.132 g/cm³ 

• Soluble in common organic solvents

Applications in Asymmetric Synthesis:

• Enolate Alkylations: Serves as an effective stereocontrolling element for highly selective enolate alkylation reactions 

• Aldol Reactions: Enables stereoselective aldol additions in complex molecule synthesis 

• Diels-Alder Cycloadditions: Used as a chiral auxiliary for asymmetric Diels-Alder reactions 

• Pharmaceutical Synthesis: An essential tool in the synthesis of complex, enantiomerically pure pharmaceuticals 

Applications:

• Pharmaceutical R&D: As a key chiral auxiliary for the asymmetric synthesis of drug candidates and enantiomerically pure intermediates

• Organic Synthesis: Used as a building block for constructing complex chiral molecules

• Analytical R&D: Serves as a reference standard for quality control (QC) and analytical method development

Packaging: ___ (e.g.: 1g, 5g, 10g, 25kg per package, as per customer's request)

Storage: Store in a cool, dry, well-ventilated area, away from direct sunlight and moisture. Recommended storage temperature: 2-8°C (Refrigerator) . For long-term storage, keep in a cool, dry place

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