28227-36-3

Usage

Class

Organic compound, Furanone derivative

Structure

Cyclic chemical structure with a furan ring

Stereochemistry

(3R)configuration

Potential applications

Pharmaceuticals, fragrances, flavors (requires further research)

Upstream product

• 108-24-7 acetic anhydride 
• 599-04-2 (R)-Pantolacton 
• 79-50-5 pantolactone 
• 75-36-5 acetyl chloride 

Downstream Products

• 599-04-2 (R)-Pantolacton 

Relevant academic research and scientific papers

Synthesis, biological activities, and docking studies of D-pantolactone derivatives as novel FAS inhibitors

A novel series of fatty acid synthase (FAS) inhibitors with D-(?)-pantolactone moiety and potential utility for the treatment of obesity were designed, synthesized and characterized, in which the structure of compound 3k was further confirmed by single X-

The assignment of the configuration for α-hydroxy acid esters using a CEC strategy

A simple and efficient 1H NMR method for determining the absolute configuration of chiral α-hydroxy acid esters using a competing enantioselective conversion (CEC) strategy was developed. The α-hydroxy acid esters were acylated in the presence

Rapid screening of hydrolases for the enantioselective conversion of 'difficult-to-resolve' substrates

Hydrolases showing high enantioselectivity towards three racemic alcohols (1-methoxy-2-propanol, 3-hydroxy-tetrahydrofuran, 3-butyn-2-ol) and pantolactone were identified by a step-wise screening procedure. Initially, those biocatalysts, which exhibited hydrolytic activity towards the corresponding acetates or butyrates, were selected out of >100 enzymes. Here, rapid screening was performed in a pH-indicator-based format in microtiter plates. Subsequently, enantioselectivity of active hydrolases was determined in small scale reactions (～1 mg substrate per reaction) by means of gas chromatography using chiral columns. Enzymes exhibiting highest enantioselectivities were then chosen for preparative scale resolution. Using this strategy, at least one suitable hydrolase was found for 3 out of the 4 model compounds examined, allowing efficient kinetic resolution. Moreover, in all cases enantiocomplementary enzymes were identified thus enabling access to both enantiomers of all substrates.

Chemistry of natural compounds and bioorganic chemistry: Enantioselectivity of enzymatic acylation of some structurally various racemic alcohols in anhydrous aprotic media

Partial acylation of (R,S)-3,7-dimethyloctan-l-ol (1) and (R,S)-7-methoxy-3,7-dimethyloctan-l-ol (2) with vinyl acetate catalyzed by the lipase from Candida cylindracea affords in good yields the corresponding S-configured acetates with 92-98% enantiomeric excess (ee). Under similar conditions, racemic α-cyclogeraniol (3), drim-7-en-11-ol, methyl 4-(3-hydroxy-2-methylpropyl)benzoate, and its η6-chromium(tricarbonyl) complex (6) are acylated with rather poor (and, for the two latter, opposite) enantioselectivity, whereas (R,S)-2,4:3,5-di-O-benzylidenexylitol remains unaffected. Racemic isoborneol (8) and 2-nitro-1-phenylethanol also remain almost or completely unconverted. Attempts to perform enantioselective acylation of alcohols 3 and 8 with Ac2O in the presence of porcine pancreatic lipase (PPL) proved equally unsuccessful. By contrast, the PPL-catalyzed acylation of alcohol 6 with vinyl acetate at 17% conversion affords the levorotatory acetate (S)-6a with ca. 100% ee. PPL-Mediated partial acylation of (R,S)-pantolactone with Ac2O, followed by mild deacylation of the resulting R acetate, gives (R)-(-)-pantolactone of 97% enantiomeric purity in 60% overall yield.

145. Analytic and Preparative Resolution on Racemic γ- and δ-Lactones by Chromatography on Cellulose Triacetate. Relationship between Elution Order and Absolute Configuration

Enantiomers of various chiral five- and six-membered-ring lactones, which are important classes of cpmpounds (flavour and pheromone components, key intermediates in the synthesis of biologically active substrates) have been separated chromatographically on the chiral phase cellulose triacetate, crystallographic form I (CTA I).Four different series of five-membered-ring lactones, relationships have been found between the elution order of the enantiomers and their absolute configuration.Preparative resolutions of γ-phenyl-γ-butyrolactone (1) and of the pheromone component 5b have been carried out to demonstrate the applicability of the method to g-scale separations.