Benzyl (2R,4R)-4-methyl-5-oxo-2-phenyl-1,3-oxazolidine-3-carboxylate

Name: Benzyl (2R,4R)-4-methyl-5-oxo-2-phenyl-1,3-oxazolidine-3-carboxylate
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CAS No. 143564-89-0
Cat. No. CS-0049901
Purity≥98%
MDL No.None

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Benzyl (2R,4R)-4-methyl-5-oxo-2-phenyl-1,3-oxazolidine-3-carboxylate|CS-0049901

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General Information

CAS No. 143564-89-0
Cat. No. CS-0049901
Purity ≥98%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₁₇NO₄
Molecular Weight 311.33
Synonym(s) (2R,4R)-4-Methyl-5-oxo-2-phenyl-3-oxazolidinecarboxylic acid phenylmethyl ester
SMILES C[C@H]1N([C@H](OC1=O)C1=CC=CC=C1)C(=O)OCC1=CC=CC=C1

Description

Benzyl (2R,4R)-4-methyl-5-oxo-2-phenyl-1,3-oxazolidine-3-carboxylate features a chiral oxazolidine core with defined stereochemistry at C2 and C4, enabling selective transformations in asymmetric synthesis. The benzyl ester group enhances solubility and stability under standard bench conditions. This scaffold serves as a key intermediate for bioactive molecule construction, particularly in peptide mimetics and kinase inhibitor development.

Application

Benzyl (2R,4R)-4-methyl-5-oxo-2-phenyl-1,3-oxazolidine-3-carboxylate serves as a stereochemically defined chiral building block for the synthesis of β-amino acid derivatives and heterocyclic scaffolds. Its oxazolidinone core enables high diastereoselective transformations, including nucleophilic ring opening and metal-catalyzed coupling reactions. The benzyl ester group offers convenient manipulation under standard deprotection conditions, while the phenyl and methyl substituents provide steric and electronic control in asymmetric synthesis. This compound is bench-stable and compatible with common organic reaction protocols.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302
Precautionary Statements : P264-P270-P330-P501

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Computational Chemistry Data

TPSA 55.84
LogP 3.2693
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Oxazolidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Benzyl (2R,4R)-4-methyl-5-oxo-2-phenyl-1,3-oxazolidine-3-carboxylate

CAS No. 143564-89-0

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