244277-48-3

Basic information

• Product Name: (-)-ETHYL (R)-2-HYDROXY-4-OXO-4-PHENYLBU
• Synonyms: (-)-ETHYL (R)-2-HYDROXY-4-OXO-4-PHENYLBU;(-)-ETHYL (R)-2-HYDROXY-4-OXO-4-PHENYLBUTYRATE, CIBA CS PROD;(alphaR)-alpha-Hydroxy-gamma-oxobenzenebutanoic acid ethyl ester
• CAS NO: 244277-48-3
• Molecular Formula: C₁₂H₁₄O₄
• Molecular Weight: 222.24
• Mol File: 244277-48-3.mol
• Article Data: 16

Chemical Properties

• Melting Point: 35-38 °C
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (-)-ETHYL (R)-2-HYDROXY-4-OXO-4-PHENYLBU(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-ETHYL (R)-2-HYDROXY-4-OXO-4-PHENYLBU(244277-48-3)
• EPA Substance Registry System: (-)-ETHYL (R)-2-HYDROXY-4-OXO-4-PHENYLBU(244277-48-3)

Safety Data

• Hazardous Substances Data: 244277-48-3(Hazardous Substances Data)

Usage

Description

(-)-ETHYL (R)-2-HYDROXY-4-OXO-4-PHENYLBU, with the molecular formula C16H16O3, is a chiral chemical compound belonging to the class of benzoyl esters. As a chiral molecule, it exists in two non-superimposable mirror image forms, or enantiomers. Its unique structure and functional groups suggest potential applications in the pharmaceutical and fine chemical industries.

Uses

Used in Pharmaceutical Industry:
(-)-ETHYL (R)-2-HYDROXY-4-OXO-4-PHENYLBU is used as an intermediate in the synthesis of pharmaceuticals for its unique structure and functional groups, which can contribute to the development of new drugs with specific therapeutic properties.
Used in Fine Chemical Industry:
In the fine chemical industry, (-)-ETHYL (R)-2-HYDROXY-4-OXO-4-PHENYLBU serves as a key component in the production of specialty chemicals, leveraging its distinctive molecular features for targeted applications.

Upstream product

• 13735-81-4 1-styrenyloxytrimethylsilane 
• 28130-07-6 N-benzoylhydroxyglycine ethyl ester 
• 6296-54-4 ethyl 2,4-dioxo-4-phenylbutyrate 
• 88330-79-4 ethyl-(Z)-2-hydroxy-4-oxo-4-phenyl-but-2-enoate 
• 208242-81-3 (R)-(-)-2-hydroxy-4-phenyl-pent-4-enoic acid ethyl ester 
• 98-83-9 isopropenylbenzene 
• 98-86-2 acetophenone 
• 91497-49-3 4-phenyl-2-hydroxy-4-oxobutyric acid ethyl ester 
• 924-44-7 glyoxylic acid ethyl ester 

Downstream Products

• 90315-82-5 ethyl (R)-2-hydroxy-4-phenylbutyrate 
• 146912-66-5 (R)-2-hydroxy-4-oxo-4-phenylbutanoic acid 
• 109010-59-5 (R)-2-<(4-nitrobenzolsulfonyl)oxy>-4-phenylbuttersaeure-ethylester 
• 162780-30-5 (+)-ethyl (S)-2-N-benzylamino-4-phenylbutyrate 
• 402587-14-8 (-)-ethyl (R)-2-hydroxy-4-cyclohexylbutyrate 
• 1215021-47-8 ethyl (R)-(-)-2-hydroxy-3-methylene-4-oxophenylbutanoate 

Relevant articles and documents

Ru-Catalyzed Chemo- and Enantioselective Hydrogenation of β-Diketones Assisted by the Neighboring Heteroatoms

A highly chemo- and enantioselective hydrogenation of β-diketones was achieved by using [Ru(benzene)(S)-SunPhosCl]Cl for consistency in THF. The neighboring heteroatoms played important roles in guaranteeing the reactivity and controlling the chemoselectivity. These results suggested a potential approach for the clean and facile synthesis of functionalized chiral β-hydroxy ketones, which could otherwise be prepared through much less step-economic transformations.

Bronsted acid catalyzed asymmetric aldol reaction: A complementary approach to enamine catalysis

A syn-enantioselective aldol reaction has been developed using Bronsted acid catalysis based on H8-BINOL-derived phosphoric acids. This method affords an efficient synthesis of various β-hydroxy ketones, some of which could not be synthesized u

Chemo-enzymatic synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate

A new biocatalytic strategy to obtain the ethyl (R)-2-hydroxy-4-oxo-4- phenylbutyrate precursor of ethyl (R)-2-hydroxy-4-phenylbutyrate, an important intermediate in the synthesis of a variety of ACE inhibitors, has been set up. Starting from ethyl 2,4-dioxo-4-phenylbutyrate, a screen of microorganisms has been performed in order to find the best catalyst able to reduce the keto group in the α-position with high chemo- and enantioselectivity. The biotransformation catalyzed by Pichia pastoris CBS 704 gave the best results in terms of conversion and enantioselectivity. The addition of adsorbing resins in the fermentation medium is effective in controlling substrate and product concentration in the medium, thus improving both conversion and enantioselectivity of the biotransformation. Preliminary experiments in a continuous batch reactor with growing culture of P. pastoris will be also presented.