131685-53-5

Basic information

• Product Name: (R)-(-)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE
• Synonyms: (R)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE;N-PROPIONYL-(4R)-BENZYL-2-OXAZOLIDINONE;N-3-PROPIONYL-(4R)-BENZYL-2-OXAZOLIDINONE;(R)-(-)-4-Benzyl-3-propiomyl-2-oxazolidinone;(4R)-4-benzyl-3-propanoyl-1,3-oxazolidin-2-one;(-)-4-Benzyl-3-propionyl-2-oxazolidinone;(4R)-4-Benzyl-3-propionyl-1,3-oxazolidin-2-one;(4R)-4-Benzyl-3-propionyloxazolidin-2-one
• CAS NO: 131685-53-5
• Molecular Formula: C₁₃H₁₅NO₃
• Molecular Weight: 233.26
• Product Categories: Oxazolidinone;chiral;Asymmetric Synthesis;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry;Peptide;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives;Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 131685-53-5.mol
• Article Data: 73

Chemical Properties

• Melting Point: 45 °C
• Boiling Point: 396.639 °C at 760 mmHg
• Flash Point: 193.681 °C
• Appearance: white to light yellow crystal powder
• Density: 1.206 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: -103 ° (C=1, EtOH)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform, Ethanol
• PKA: -2.35±0.40(Predicted)
• CAS DataBase Reference: (R)-(-)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE(131685-53-5)
• EPA Substance Registry System: (R)-(-)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE(131685-53-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 131685-53-5(Hazardous Substances Data)

Usage

Description

(R)-(-)-4-Benzyl-3-Propionyl-2-Oxazolidinone is an oxazolidinone derivative characterized by its white to light yellow crystal powder form. It serves as a versatile building block in organic synthesis, particularly for the preparation of various oxazolidinone derivatives.

Uses

Used in Pharmaceutical Industry:
(R)-(-)-4-Benzyl-3-Propionyl-2-Oxazolidinone is used as a key intermediate in the synthesis of anisomycin analogues, which act as activators of the JNK/SAPK1 and p38/SAPK2 pathways. These pathways play a crucial role in cellular processes such as apoptosis, inflammation, and immune responses, making this compound valuable in the development of pharmaceuticals targeting these pathways.
Used in Organic Synthesis:
(R)-(-)-4-Benzyl-3-Propionyl-2-Oxazolidinone is used as a building block for the preparation of complex organic molecules. One such application is in the synthesis of methyl 3-[(S)-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methyl-3-oxopropyl]benzoate. This is achieved by treating the compound with a strong base, followed by the addition of methyl 3-bromomethyl benzoate, showcasing its utility in creating diverse chemical structures for various applications.

InChI:InChI=1/C13H15NO3/c1-2-12(15)14-11(9-17-13(14)16)8-10-6-4-3-5-7-10/h3-7,11H,2,8-9H2,1H3/t11-/m1/s1

Upstream product

• 352438-07-4 ⁽⁴⁵⁾-3-propionyl-4-benzyl-2-oxazolidinone 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 
• 123-62-6 propionic acid anhydride 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 79-03-8 propionyl chloride 
• 105-58-8 Diethyl carbonate 
• 152899-14-4 <3(2'S),4S>-3-(2-Methyl-1-oxooctyl)-4-(phenylmethyl)-2-oxazolidinone 
• 152899-15-5 <3(2'R),4S>-3-(2-Methyl-1-oxooctyl)-4-(phenylmethyl)-2-oxazolidinone 
• 152899-13-3 (4S)-4-benzyl-3-octanoyl-1,3-oxazolidin-2-one 
• 3182-95-4 L-Phenylalaninol 
• 63-91-2 L-phenylalanine 
• 133467-37-5 (4S)-3-[(2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoyl]-4-benzyl-2-oxazolidinone 
• 220170-24-1 C₈H₁₄O₃ 
• 802294-64-0 propionic acid 

Downstream Products

• 139278-19-6 <3(2S,3R)4S>-3-<3-hydroxy-2-methyl-6-heptenoyl>-4-benzyl-2-oxazolidinone 
• 136546-77-5 (4R)-5-[(4S)-4-benzyl-2-oxooxazolidin-3-yl]-4-methyl-5-oxopentanenitrile 
• 136546-77-5 (S)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-4-methyl-5-oxo-pentanenitrile 
• 192864-91-8 (4S)-4-benzyl-3-(2-bromopropanoyl)-1,3-oxazolidin-2-one 
• 169218-76-2 <3(2S,3S),4S>-4-Benzyl-3-<4-chloro-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-1-oxobutyl>-2-oxazolidinone 
• 169218-76-2 <3(2R,3S),4S>-4-Benzyl-3-<4-chloro-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-1-oxobutyl>-2-oxazolidinone 
• 169218-76-2 <3(2S,3R),4S>-4-Benzyl-3-<4-chloro-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-1-oxobutyl>-2-oxazolidinone 
• 169218-76-2 <3(2R,3R),4S>-4-Benzyl-3-<4-chloro-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-1-oxobutyl>-2-oxazolidinone 
• 177767-29-2 (3(2S,4R)4R)-3-(2,4-dimethyloctanoyl)-4-benzyl-2-oxazolidinone 
• 177607-84-0 (3(2S,4S)4R)-3-(2,4-dimethyloctanoyl)-4-benzyl-2-oxazolidinone 
• 197227-61-5 (S)-4-benzyl-3-[(2S,3R)-4-cyclopent-3-enyl-3-hydroxy-2-methylbutanoyl]-oxazolidin-2-one 
• 116996-56-6 (4S)-4-benzyl-3-[(2R)-2-methylpent-4-enoyl]oxazolidin-2-one 
• 202874-73-5 (4S)-3-((2R)-4-(tert-butoxy)-2-methyl-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one 
• 131832-48-9 (4S)-4-benzyl-3-[(2S,3R)-3-hydroxy-2,4-dimethylpentanoyl]oxazolidin-2-one 

Relevant articles and documents

Thermal proteome profiling efficiently identifies ribosome destabilizing oxazolidinones

Identifying the targets of bioactive small molecules is a challenging endeavor for which no general solution currently exists. Classical affinity purification experiments suffer from the need to functionalise a bioactive compound and link it to a solid support, which may interfere with target binding. A modern mass spectrometry-based proteomics technique that has partially circumvented this problem is thermal proteome profiling (TPP), which determines the effect of an unmodified small molecule on the thermal stability of the whole proteome simultaneously. Here, we use TPP to identify the mode-of-action of a newly-discovered autophagy inhibitor based on oxazolidinones often employed as chiral auxiliaries. Surprisingly, a significant portion of all ribosomal proteins were found to be destabilized by the inhibitor, highlighting the utility of this technology for determining a challenging mode-of-action.

Synthesis and Bioactivity of a Macrocidin B Stereoisomer

A stereoisomer of macrocidin B, a presumed metabolite of the fungus Phoma macrostoma, was synthesized in 18 steps and 2.7% yield from protected l-tyrosine that was N-β-ketoacylated with a fully functionalized octanoyl Meldrum's acid. Dieckmann condensation gave a 3-acyltetramic acid, which was macrocyclized via Williamson etherification between the phenol and epi-bromohydrin termini. This macrocidin B stereoisomer showed a weaker herbicidal effect than macrocidin A and no similar inhibitory effect on biofilms of Staphylococcus aureus.

Ring-closing metathesis approaches towards the total synthesis of rhizoxins

Efforts are described towards the total synthesis of the bacterial macrolide rhizoxin F, which is a potent tubulin assembly and cancer cell growth inhibitor. A significant amount of work was expanded on the construction of the rhizoxin core macrocycle by ring-closing olefin metathesis (RCM) between C(9) and C(10), either directly or by using relay substrates, but in no case was ringclosure achieved. Macrocycle formation was possible by ring-closing alkyne metathesis (RCAM) at the C(9)/C(10) site. The requisite diyne was obtained from advanced intermediates that had been prepared as part of the synthesis of the RCM substrates. While the direct conversion of the triple bond formed in the ring-closing step into the C(9)-C(10) E double bond of the rhizoxin macrocycle proved to be elusive, the corresponding Z isomer was accessible with high selectivity by reductive decomplexation of the biscobalt hexacarbonyl complex of the triple bond with ethylpiperidinium hypophosphite. Radical-induced double bond isomerization, full elaboration of the C(15) side chain, and directed epoxidation of the C(11)-C(12) double bond completed the total synthesis of rhizoxin F.