(S)-Benzyl 3-(2,5-dioxooxazolidin-4-yl)propanoate

Name: (S)-Benzyl 3-(2,5-dioxooxazolidin-4-yl)propanoate
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 3190-71-4
Cat. No. CS-W005557
Purity≥97%
MDL No.MFCD11046651

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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(S)-Benzyl 3-(2,5-dioxooxazolidin-4-yl)propanoate|CS-W005557

Structure of 3190-71-4

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General Information

CAS No. 3190-71-4
Cat. No. CS-W005557
Purity ≥97%
MDL No. MFCD11046651
Storage -20°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₃NO₅
Molecular Weight 263.25
Synonym(s) Glutamic acid,5-benzyl ester,NCA
SMILES O=C(CC[C@@H]1NC(=O)OC1=O)OCC1=CC=CC=C1

Description

(S)-Benzyl 3-(2,5-dioxooxazolidin-4-yl)propanoate is a chiral building block featuring a stereodefined oxazolidinone ring fused to a propanoate side chain. This scaffold delivers high enantiocontrol in asymmetric synthesis, particularly in transition-metal-catalyzed conjugate additions and cycloadditions. The benzylic ester group enables selective derivatization under mild conditions. Its bench-stable nature supports reliable handling in synthetic workflows.

Application

(S)-Benzyl 3-(2,5-dioxooxazolidin-4-yl)propanoate serves as a versatile chiral synthon in asymmetric synthesis, enabling efficient construction of β-amino acid derivatives and oxazolidinone-containing scaffolds. The protected amino group exhibits excellent functional group tolerance and bench stability, facilitating straightforward transformations in multistep sequences. Its well-defined stereochemistry supports high diastereoselectivity in downstream reactions, making it a reliable building block for medicinal chemistry and peptide analog development.

Synthesis

Route1
- In-stock
  
  1676-73-9
- ~90%
- In-stock
  
  3190-71-4
References
- SIGMA-ALDRICH CO. Patent: WO2006/47703 A2, 2006 ; Location in patent: Page/Page column 12-13 ;
Route2
- 75-44-5
- In-stock
  
  1676-73-9
- ~96%
- In-stock
  
  3190-71-4
References
- Sill, Kevin; Vojkovsky, Tomas; Carie, Adam Patent: US2013/280306 A1, 2013 ; Location in patent: Paragraph 0394; 0395 ;
Route3
- 32315-10-9
- In-stock
  
  1676-73-9
- ~92%
- In-stock
  
  3190-71-4
References
- Whitton, Greg; Gauthier, Mario Journal of Polymer Science, Part A: Polymer Chemistry, 2013 , vol. 51, # 24 p. 5270 - 5279

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 81.7
LogP 1.145
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 5

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

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Peptide Chemistry Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Amino Acid Derivatives

Key Words

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(S)-Benzyl 3-(2,5-dioxooxazolidin-4-yl)propanoate

CAS No. 3190-71-4

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