474828-48-3

Basic information

• Product Name: (4R)-3-[(2R)-2-Methyl-1-oxobutyl]-4-(phenylMethyl)-2-oxazolidinone
• Synonyms: (4R)-3-[(2R)-2-Methyl-1-oxobutyl]-4-(phenylMethyl)-2-oxazolidinone
• CAS NO: 474828-48-3
• Molecular Formula: C₁₅H₁₉NO₃
• Molecular Weight: 261.31626
• Product Categories: Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 474828-48-3.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Solubility: DCM, Ethyl Acetate, Methanol
• CAS DataBase Reference: (4R)-3-[(2R)-2-Methyl-1-oxobutyl]-4-(phenylMethyl)-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (4R)-3-[(2R)-2-Methyl-1-oxobutyl]-4-(phenylMethyl)-2-oxazolidinone(474828-48-3)
• EPA Substance Registry System: (4R)-3-[(2R)-2-Methyl-1-oxobutyl]-4-(phenylMethyl)-2-oxazolidinone(474828-48-3)

Safety Data

• Hazardous Substances Data: 474828-48-3(Hazardous Substances Data)

Usage

Description

(4R)-3-[(2R)-2-Methyl-1-oxobutyl]-4-(phenylMethyl)-2-oxazolidinone is a complex organic compound with a unique molecular structure, characterized by its oxazolidinone ring and various substituents. It is a chiral molecule with specific stereochemistry, which is important for its potential applications.

Uses

Used in Pharmaceutical Industry:
(4R)-3-[(2R)-2-Methyl-1-oxobutyl]-4-(phenylMethyl)-2-oxazolidinone is used as an intermediate in the synthesis of (R)-2-Methylbutyric Acid (M294365), a compound with potential therapeutic applications. Its role in the synthesis process is crucial for the production of the final pharmaceutical product, highlighting its importance in the development of new medications.

Upstream product

• 111292-87-6 (R)-3-(1-butyryl)-4-benzyloxazolidine-2-one 
• 74-88-4 methyl iodide 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 

Downstream Products

• 616-16-0 (R)-2-Methyl-1-butanol 
• 46481-05-4 (R)-2-methyl-1-butanol 4-methylbenzenesulfonate 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 
• 101711-78-8 (3R)-3-propionyl-4-benzyloxazolidin-2-one 
• 1501971-58-9 (4R)-4-benzyl-3-((2R,3S,4R)-3-hydroxy-2,4-dimethylhexanoyl)oxazolidin-2-one 
• 1501971-59-0 (2R,3S,4R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2,4-dimethyl-1-oxohexan-3-yl-4-methylbenzenesulfonate 
• 1094390-39-2 pre-tenellin B 
• 36272-22-7 (R)-(+)-2-methylbutylamine 
• 1565-80-6 (2S)-2-methyl-1-butanol 

Relevant articles and documents

Asymmetric total synthesis of four stereoisomers of the sex pheromone of the western corn rootworm

A convergent synthesis of four stereoisomers of the sex pheromone of the western corn rootworm (8-methyldecan-2-yl propionate, 1) from commercially available chiral starting materials is reported. The key step was Julia–Kocienski olefination between chiral BT-sulfone and chiral aldehyde. This synthetic route provided the four stereoisomers of 1 in 24–29% total yield via a six-step sequence. The simple scale-up strategy provides a new way to achieve the asymmetric synthesis of the sex pheromone.

Stereoselective synthesis of the Paulownia bagworm sex pheromone

According to our retrosynthesis, the main chain of the target molecule could be constructed using a C5?+?C7?+?C5 strategy. The key induction reaction afforded chiral methyl group moieties using different Evans templates with different configurations. Li2CuCl4 was effectively employed in the Csp3[sbnd]Csp3 coupling protocol. The target molecular was obtained in a 12.6% overall yield with nine steps in the longest linear route.

Rational Design of Thermodynamic and Kinetic Binding Profiles by Optimizing Surface Water Networks Coating Protein-Bound Ligands

A previously studied congeneric series of thermolysin inhibitors addressing the solvent-accessible S2′ pocket with different hydrophobic substituents showed modulations of the surface water layers coating the protein-bound inhibitors. Increasing stabilization of water molecules resulted in an enthalpically more favorable binding signature, overall enhancing affinity. Based on this observation, we optimized the series by designing tailored P2′ substituents to improve and further stabilize the surface water network. MD simulations were applied to predict the putative water pattern around the bound ligands. Subsequently, the inhibitors were synthesized and characterized by high-resolution crystallography, microcalorimetry, and surface plasmon resonance. One of the designed inhibitors established the most pronounced water network of all inhibitors tested so far, composed of several fused water polygons, and showed 50-fold affinity enhancement with respect to the original methylated parent ligand. Notably, the inhibitor forming the most perfect water network also showed significantly prolonged residence time compared to the other tested inhibitors.