(4S,5R)-(-)-4-Methyl-5-phenyl-2-oxazolidinone | CAS 16251-45-9 | Chiral Auxiliary for Asymmetric Synthesis

Product Details

Product Name: (4S,5R)-(-)-4-Methyl-5-phenyl-2-oxazolidinone

CAS No.: 16251-45-9

Synonyms: (4S,5R)-4-Methyl-5-phenyloxazolidin-2-one; (4S,5R)-4-Methyl-5-phenyl-1,3-oxazolidin-2-one; cis-4-Methyl-5-phenyloxazolidin-2-one

Molecular Formula: C₁₀H₁₁NO₂

Molecular Weight: 177.20 g/mol

MDL Number: MFCD00066226

Appearance: White to off-white crystalline powder or solid

Melting Point: 121–123 °C (lit.)

Specific Rotation: [α]²⁵/D = −168° (c = 2, chloroform)

Assay/Purity: ≥97% (typical commercial grade; higher purity available upon request)

Description:

(4S,5R)-(-)-4-Methyl-5-phenyl-2-oxazolidinone is a chiral oxazolidinone compound widely used as a versatile chiral auxiliary in asymmetric organic synthesis . Its rigid five-membered ring structure, bearing a methyl group at the 4-position and a phenyl group at the 5-position, effectively controls facial selectivity in a wide range of stereoselective transformations, including aldol reactions, alkylations, and cycloadditions .

This compound has been successfully employed as a key chiral building block in the total synthesis of natural products such as (+)-pumiliotoxin B, and serves as an important intermediate in pharmaceutical research and development . It functions as a highly effective chiral auxiliary for the preparation of enantiopure compounds and is a reagent of choice for laboratory chiral synthesis projects .

Applications:

Asymmetric Synthesis: Used as a chiral auxiliary/inducer for the preparation of compounds containing chiral centers

Pharmaceutical Intermediates: Key intermediate in the synthesis of antibiotics and other pharmaceutical actives; aids in the synthesis of single stereochemical drug molecules

Research Reagent: Employed in organic synthesis methodology research to study chiral induction mechanisms and optimize reaction conditions

Natural Product Synthesis: Utilized in the total synthesis of complex natural products including pumiliotoxins

Storage: Store in a tightly sealed container in a cool, dry place, away from direct sunlight. Room temperature storage is suitable .

Safety Information (GHS):

Signal Word: Warning

Hazard Statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation)

Precautionary Statements: P264, P280, P302+P352, P305+P351+P338