(R)-4-Phenyloxazolidin-2-one

Name: (R)-4-Phenyloxazolidin-2-one
Brand: ChemScene
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CAS No. 90319-52-1
Cat. No. CS-W017924
Purity≥97%
MDL No.MFCD00192393

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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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Structure of 90319-52-1

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General Information

CAS No. 90319-52-1
Cat. No. CS-W017924
Purity ≥97%
MDL No. MFCD00192393
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₉NO₂
Molecular Weight 163.17
Synonym(s) 2-Oxazolidinone, 4-Phenyl-, (R)-
SMILES O=C1OC[C@@H](C2=CC=CC=C2)N1

Description

Used for -amino acid synthesis and the preparation of -lactam antibiotics.

Application

(R)-4-Phenyloxazolidin-2-one serves as a robust chiral auxiliary in asymmetric synthesis, enabling stereoselective enolate alkylations and aldol reactions. Its bench-stable nature and high diastereoselectivity facilitate efficient construction of complex α-hydroxy and α-amino acid derivatives. The oxazolidinone ring functions as a reliable directing group in transition-metal-catalyzed transformations and supports orthogonal protection strategies in peptide and natural product synthesis.

Synthesis

Route1
- 201230-82-2
- In-stock
  
  56613-80-0
- ~87%
- In-stock
  
  90319-52-1
References
- Gabriele, Bartolo; Salerno, Giuseppe; Brindisi, Donatella; Costa, Mirco; Paolo Chiusoli, Gian Organic Letters, 2000 , vol. 2, # 5 p. 625 - 626
Route2
- 214492-02-1
- ~93%
- In-stock
  
  7782-24-3
- In-stock
  
  90319-52-1
References
- Tetrahedron Asymmetry, , vol. 22, # 4 p. 439 - 463
Route3
- 124-38-9
- In-stock
  
  56613-80-0
- ~92%
- In-stock
  
  90319-52-1
References
- Paz, Jairo; Perez-Balado, Carlos; Iglesias, Beatriz; Munoz, Luis Journal of Organic Chemistry, 2010 , vol. 75, # 9 p. 3037 - 3046

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 38.33
LogP 1.4675
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Auxiliaries

Building Blocks Skeleton Aliphatic heterocycle compounds Oxazolidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Catalysis Asymmetric Synthesis Chiral Auxiliaries

Key Words

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(R)-4-Phenyloxazolidin-2-one

CAS No. 90319-52-1

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