55094-99-0

Basic information

• Product Name: (S)-2-Hydroxypentanedioic Acid Diethyl Ester
• Synonyms: (S)-2-Hydroxypentanedioic Acid Diethyl Ester;(2S)-2-Hydroxypentanedioic Acid 1,5-Diethyl Ester
• CAS NO: 55094-99-0
• Molecular Formula: C₉H₁₆O₅
• Molecular Weight: 204.22034
• Product Categories: Aliphatics;Chiral Reagents
• Mol File: 55094-99-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-2-Hydroxypentanedioic Acid Diethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Hydroxypentanedioic Acid Diethyl Ester(55094-99-0)
• EPA Substance Registry System: (S)-2-Hydroxypentanedioic Acid Diethyl Ester(55094-99-0)

Safety Data

• Hazardous Substances Data: 55094-99-0(Hazardous Substances Data)

Usage

Description

(S)-2-Hydroxypentanedioic Acid Diethyl Ester, also known as a derivative of 2-hydroxyglutaric acid, is an organic compound with the molecular formula C9H16O5. It is characterized by its ester functional group and hydroxyl group, which contribute to its unique chemical properties and potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
(S)-2-Hydroxypentanedioic Acid Diethyl Ester is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
(S)-2-Hydroxypentanedioic Acid Diethyl Ester is used as a building block in the synthesis of enantiomers of 4-substituted γ-lactones. These γ-lactones are important structural motifs found in various biologically active compounds, making this ester a valuable precursor in the development of novel pharmaceuticals and other bioactive molecules.

Upstream product

• 64-17-5 ethanol 
• 13095-48-2 L-hydroxyglutaric acid 
• 5965-53-7 diethyl 2-ketoglutarate 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 328-50-7 α-ketoglutaric acid 
• 56-86-0 L-glutamic acid 

Downstream Products

• 5470-86-0 (S)-1,2,5-triacetoxy-pentane 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 32780-07-7 (S)-5-(benzoyloxymethyl)tetrahydrofuran-2-one 
• 259523-52-9 (S)-5-(benzoyloxymethyl-3-[(E)-(dimethylamino)methylidene])tetrahydrofuran-2-one 
• 75073-51-7 5,5-dideuterio-4-(3',3'-dideuterio-3'-p-tolylsulphonyloxypropyl)-2,2-dimethyl-1,3-dioxolan 

Relevant articles and documents

Biotechnological properties of sponges from northeast Brazil: Cliona varians as a Biocatalyst for Enantioselective Reduction of Carbonyl Compounds

To research the potential ability of whole marine sponges to act as biocatalysts, this paper describes for the first time the employment of whole Cliona varians sponge in the stereoselective reduction of prochiral α-keto esters and isatin to the corresponding chiral alcohols. The addition of D-fructose, D-glucose or sucrose remarkably increased the conversion ratios and stereoselectivities by this marine sponge. Furthermore, in the presence of D-glucose and D-maltose, the reduction of isatin by C. varians afforded the corresponding 3-hydroxyindolin-2-one with high conversions (85-90percent) and good enantioselectivities (60-74percent). These results showed that the marine sponge presents great potential to be used as biocatalyst for stereoselective reduction of carbonyl compounds.

Synthesis of (S)-3-heteroaryl-2-hydroxy-1-propyl benzoates by 'ring switching' methodology

(S)-5-Benzoyloxymethyl-3-[(E)-(dimethylamino)methylidene]tetrahydrofuran-2- one (6), prepared in 5 steps from L-glutamic acid (1), was used as precursor in a one step 'ring switching' synthesis of (S)-2-hydroxy-3-heteroaryl-1-propyl benzoates 13-18, 23, 24. In the reaction of 6 with 2-aminopyridine (21) and 2-amino-4,6-dimethylpyrimidine (22) the corresponding dimethylamine substitution products (25, 26) were obtained.

Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates

Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic γ-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products.