(4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid

Name: (4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid
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CAS No. 196404-55-4
Cat. No. CS-0022809
Purity≥96%
MDL No.MFCD09837613

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(4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid|CS-0022809

Structure of 196404-55-4

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General Information

CAS No. 196404-55-4
Cat. No. CS-0022809
Purity ≥96%
MDL No. MFCD09837613
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₂H₂₅NO₆
Molecular Weight 399.44
Synonym(s) (4S,5R)-3-tert-butoxycarbony-2-(4-anisyl)-4-phenyl-5-oxazolidinercarboxylicacid
SMILES CC(C)(C)OC(N1[C@@H](C2=CC=CC=C2)[C@H](C(O)=O)OC1C3=CC=C(OC)C=C3)=O

Description

This oxazolidine derivative features a chiral scaffold with orthogonal functional handles: a tert-butoxycarbonyl group for selective protection and a para-methoxyphenyl moiety enhancing solubility. The carboxylic acid enables direct conjugation or derivatization, while the phenyl substituent imparts rigidity and steric control. Designed for use in asymmetric synthesis and peptide mimetic construction under standard bench conditions.

Application

This chiral oxazolidine serves as a robust building block for the synthesis of bioactive heterocycles and peptidomimetics. Its well-defined stereochemistry enables predictable transformations, while the Boc-protected carboxylic acid and pendant aryl groups offer orthogonal functionality for sequential coupling reactions. Bench-stable and readily purified by chromatography, it facilitates efficient access to complex scaffolds in medicinal chemistry campaigns.

Synthesis

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References
- Bioorganic and Medicinal Chemistry, , vol. 22, # 1 p. 194 - 203
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  670254-71-4
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References
- Journal of Heterocyclic Chemistry, , vol. 42, # 4 p. 679 - 684
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  24424-99-5
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References
- Journal of Heterocyclic Chemistry, , vol. 42, # 4 p. 679 - 684

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 85.3
LogP 4.1556
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 4

Other Classifications

Bioactive Molecules Natural Products

Building Blocks Functional Group Boc

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Oxazolidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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(4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid

CAS No. 196404-55-4

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