243658-52-8

Basic information

• Product Name: (+)-ETHYL (S)-2-HYDROXY-4-OXO-4-PHENYLBU
• Synonyms: (+)-ETHYL (S)-2-HYDROXY-4-OXO-4-PHENYLBU;(+)-ETHYL (S)-2-HYDROXY-4-OXO-4-PHENYLBUTYRATE, CIBA CS PROD;(alphaS)-alpha-Hydroxy-gamma-oxobenzenebutanoic acid ethyl ester
• CAS NO: 243658-52-8
• Molecular Formula: C₁₂H₁₄O₄
• Molecular Weight: 222.239
• Mol File: 243658-52-8.mol
• Article Data: 17

Chemical Properties

• Melting Point: 35-38 °C
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (+)-ETHYL (S)-2-HYDROXY-4-OXO-4-PHENYLBU(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-ETHYL (S)-2-HYDROXY-4-OXO-4-PHENYLBU(243658-52-8)
• EPA Substance Registry System: (+)-ETHYL (S)-2-HYDROXY-4-OXO-4-PHENYLBU(243658-52-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 243658-52-8(Hazardous Substances Data)

Usage

Description

(+)-ETHYL (S)-2-HYDROXY-4-OXO-4-PHENYLBU, also known as ethyl (S)-2-hydroxy-4-oxo-4-phenylbutanoate, is a chiral chemical compound with a molecular formula of C12H14O4. It is characterized by its specific stereochemistry and is commonly utilized in pharmaceutical research and drug development. (+)-ETHYL (S)-2-HYDROXY-4-OXO-4-PHENYLBU may possess various biological activities and serves as a precursor for synthesizing other compounds. It is crucial to handle and use (+)-ETHYL (S)-2-HYDROXY-4-OXO-4-PHENYLBU with care, adhering to safety protocols and considering regulatory requirements and restrictions.

Uses

Used in Pharmaceutical Research and Drug Development:
(+)-ETHYL (S)-2-HYDROXY-4-OXO-4-PHENYLBU is used as a chiral building block for the synthesis of pharmaceutical compounds, contributing to the development of new drugs with improved efficacy and selectivity. Its unique stereochemistry allows for the creation of enantiomerically pure compounds, which is essential for ensuring the desired biological activity and minimizing potential side effects.
Used as a Precursor in Organic Synthesis:
In the field of organic synthesis, (+)-ETHYL (S)-2-HYDROXY-4-OXO-4-PHENYLBU serves as a valuable precursor for the preparation of various organic compounds. Its functional groups and chiral center enable the formation of a wide range of derivatives, which can be further utilized in the synthesis of complex molecules and materials.
Used in the Synthesis of Biologically Active Compounds:
Due to its potential biological activities, (+)-ETHYL (S)-2-HYDROXY-4-OXO-4-PHENYLBU can be employed as a starting material for the synthesis of biologically active compounds. These compounds may have applications in various therapeutic areas, including but not limited to, anti-inflammatory, antimicrobial, and anticancer agents.

Upstream product

• 924-44-7 glyoxylic acid ethyl ester 
• 697301-71-6 (1-phenylvinyl)carbamic acid benzyl ester 
• 98-86-2 acetophenone 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 72328-04-2 methyl 1-phenylvinylcarbamate 
• 88330-79-4 ethyl-(Z)-2-hydroxy-4-oxo-4-phenyl-but-2-enoate 
• 6296-54-4 ethyl 2,4-dioxo-4-phenylbutyrate 
• 28130-07-6 N-benzoylhydroxyglycine ethyl ester 

Downstream Products

• 125639-64-7 (S)-ethyl 2-hydroxy-4-phenylbutyrate 
• 115016-95-0 (S)-2-hydroxy-4-phenylbutanoic acid 
• 402587-14-8 (+)-ethyl (S)-2-hydroxy-4-cyclohexylbutyrate 
• 146912-63-2 (S)-2-hydroxy-4-oxo-4-phenylbutanoic acid 

Relevant articles and documents

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.

New technical synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate of high enantiomeric purity

A new technical synthesis to produce ethyl (R)-2-hydroxy-4-phenylbutyrate (5), an important intermediate for several ACE inhibitors with >99% ee in an over-all yield of 50-60% is described starting from acetophenone and diethyl oxalate. Key step is the chemo- and enantioselective hydrogenation of ethyl 2,4-dioxo-4-phenylbutyrate (6) (ee up to 86%) catalyzed by a heterogeneous Pt catalyst modified with dihydrocinchonidine, followed by crystallization of the 2-hydroxy-4-oxo ester 7 and hydrogenolysis of the 4-keto group. (C) 2000 Elsevier Science Ltd.

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