132076-32-5

Usage

Uses

Used in Pharmaceutical Synthesis:
Cyclopentanecarboxylic acid, 3-oxo-, methyl ester, (S)(9CI) is used as a synthetic intermediate for the development of pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block in the synthesis of various drugs, particularly those targeting specific medical conditions.
Used in Drug Development:
In the pharmaceutical industry, Cyclopentanecarboxylic acid, 3-oxo-, methyl ester, (S)(9CI) is used as a key component in the development of new drugs. Its versatile structure allows for the creation of a wide range of drug candidates, which can be further modified and optimized to enhance their therapeutic properties.
Used in Medicinal Chemistry Research:
Cyclopentanecarboxylic acid, 3-oxo-, methyl ester, (S)(9CI) is also utilized in medicinal chemistry research to study the structure-activity relationships of various drug candidates. By understanding how Cyclopentanecarboxylic acid, 3-oxo-, methyl ester, (S)- (9CI) interacts with biological targets, researchers can design more effective and selective drugs with improved pharmacological profiles.
Used in Drug Delivery Systems:
In addition to its role in drug synthesis, Cyclopentanecarboxylic acid, 3-oxo-, methyl ester, (S)(9CI) can also be employed in the development of drug delivery systems. Its unique properties may allow for the creation of novel drug carriers that can improve the bioavailability, targeting, and overall efficacy of pharmaceutical compounds.

Upstream product

• 3212-60-0 cyclopent-2-enol 
• 201230-82-2 carbon monoxide 
• 149-73-5 trimethyl orthoformate 
• 25662-28-6 1-(carboxymethoxy)cyclopentadiene 
• 162086-59-1 3-hydroxy-cyclopentene-1-carboxylic acid methyl ester 
• 71830-06-3 (-)-(S)-3-oxocyclopentanecarboxylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 108384-35-6 methyl 3-oxocyclopent-1-enecarboxylate 
• 98-78-2 3-Oxo-cyclopentanecarboxylic acid 
• 67-56-1 methanol 

Relevant academic research and scientific papers

Asymmetric Synthesis of N-Substituted γ-Amino Esters and γ-Lactams Containing α,γ-Stereogenic Centers via a Stereoselective Enzymatic Cascade

γ-Amino esters and γ-lactams containing α,γ-stereogenic centers are widely used as chiral intermediates in various bioactive compounds, while their efficient synthesis remains a challenge. Herein, an enzymatic cascade reaction involving an ene reductase (

A robust and stereocomplementary panel of ene-reductase variants for gram-scale asymmetric hydrogenation

We report an engineered panel of ene-reductases (ERs) from Thermus scotoductus SA-01 (TsER) that combines control over facial selectivity in the reduction of electron deficient C[dbnd]C double bonds with thermostability (up to 70 °C), organic solvent tolerance (up to 40 % v/v) and a broad substrate scope (23 compounds, three new to literature). Substrate acceptance and facial selectivity of 3-methylcyclohexenone was rationalized by crystallisation of TsER C25D/I67T and in silico docking. The TsER variant panel shows excellent enantiomeric excess (ee) and yields during bi-phasic preparative scale synthesis, with isolated yield of up to 93 % for 2R,5S-dihydrocarvone (3.6 g). Turnover frequencies (TOF) of approximately 40 000 h?1 were achieved, which are comparable to rates in hetero- and homogeneous metal catalysed hydrogenations. Preliminary batch reactions also demonstrated the reusability of the reaction system by consecutively removing the organic phase (n-pentane) for product removal and replacing with fresh substrate. Four consecutive batches yielded ca. 27 g L?1 R-levodione from a 45 mL aqueous reaction, containing less than 17 mg (10 μM) enzyme and the reaction only stopping because of acidification. The TsER variant panel provides a robust, highly active and stereocomplementary base for further exploitation as a tool in preparative organic synthesis.

Biocatalytic synthesis of chiral cyclic γ-oxoesters by sequential C-H hydroxylation, alcohol oxidation and alkene reduction

A three-step biocatalytic procedure is described for the conversion of methyl and ethyl cyclopentene- and cyclohexenecarboxylates into both the enantiomers of the corresponding chiral 3-oxoesters, which are useful building blocks for the synthesis of active pharmaceutical ingredients. The allylic hydroxylation of the starting cycloalkenecarboxylates is carried out by using R. oryzae resting cells entrapped in alginate beads, in acetate buffer solution at 25 °C. The oxidation of the intermediate allylic alcohols to unsaturated ketones, performed by the laccase/TEMPO system, and the ene-reductase mediated hydrogenation of the alkene bond were carried out in the same reaction vessel in a sequential mode at 30 °C. Being entirely biocatalytic, our multistep procedure provides considerable advantages in terms of selectivity and environmental impact over reported chemical methods.

Biocatalytic access to nonracemic γ-oxo esters: Via stereoselective reduction using ene-reductases

The asymmetric bioreduction of α,β-unsaturated γ-keto esters using ene-reductases from the Old Yellow Enzyme family proceeds with excellent stereoselectivity and high conversion levels, covering a broad range of acyclic and cyclic derivatives. Various strategies were employed to provide access to both enantiomers, which are versatile precursors of bioactive molecules. The regioselectivity of hydride addition on di-activated alkenes was elucidated by isotopic labeling experiments and showed strong preference for the keto moiety as activating/binding group as opposed to the ester. Finally, chemoenzymatic synthesis of (R)-2-(2-oxocyclohexyl)acetic acid was achieved in high ee on a preparative scale combining enzymatic reduction followed by ester hydrogenolysis.

2,2-DIFLUORODIOXOLO A2A RECEPTOR ANTAGONISTS

The present invention is directed to 2,2-difluorodioxolo compounds that are antagonists of A2A receptor. The present invention is also directed to uses of the 2,2-difluorodioxolo compounds described herein in the potential treatment or prevention of neurological disorders and diseases in which A2A receptor are involved. The present invention is also directed to pharmaceutical compositions comprising these compounds and to uses of these pharmaceutical compositions in the prevention or treatment of such diseases in which A2A receptors are involved.

2,2-DIFLUORODIOXOLO A2A RECEPTOR ANTAGONISTS

The present invention is directed to 2,2-difluorodioxolo compounds that are antagonists of A2A receptor. The present invention is also directed to uses of the 2,2- difluorodioxolo compounds described herein in the potential treatment or prevent

Palladium(II)-catalyzed dicarboxymethylation of chiral allylic alcohols: Chirality transfer affording optically active diesters containing three contiguous chiral centers

This manuscript describes the extension of Stille's palladium-catalyzed olefin dicarbonylation reaction to chiral allylic alcohols with chirality transfer to afford the corresponding chiral alcohol functionalized with bis-carbomethoxy esters, containing three contiguous chiral centers, in good to excellent diastereoselectivities (78-98%).

Directed evolution of an enantioselective enoate-reductase: Testing the utility of iterative saturation mutagenesis

Directed evolution utilizing iterative saturation mutagenesis (ISM) has been applied to the old yellow enzyme homologue YqjM in the quest to broaden its substrate scope, while controlling the enantioselectivity in the bioreduction of a set of substituted cyclopentenone and cyclohexenone derivatives. Guided by the known crystal structure of YqjM, 20 residues were selected as sites for saturation mutagenesis, a pooling strategy based on the method of Phizicky [M. R. Martzen, S. M. McCraith, S. L. Spinelli, F. M. Torres, S. Fields, E. J. Grayhack, E. M. Phizicky, Science 1999, 286, 1153-1155] being used in the GC screening process. The genes of some of the hits were subsequently employed as templates for randomization experiments at the other putative hot spots. Both (R)-and (S)-selective variants were evolved using 3-methylcyclohexenone as the model substrate in the asymmetric bioreduction of the olefinic functionality, only small mutant libraries and thus minimal screening effort being necessary. Some of the best mutants also proved to be excellent catalysts when testing other prochiral substrates without resorting to additional mutagenesis/screening experiments. Thus, the results constitute an important step forward in generalizing the utility of ISM as an efficient method in laboratory evolution of enzymes as catalysts in organic chemistry.

Hydride reduction of alpha, beta-unsaturated carbonyl compounds using chiral organic catalysts

Nonmetallic, chiral organic catalysts are used to catalyze the 1,4-hydride reduction of an α,β-unsaturated carbonyl compound. The α,β-unsaturated carbonyl compound may be an aldehyde or cyclic ketone, and the hydride donor may be a dihydropyridine. The reaction is enantioselective, and proceeds with a variety of hydride donors, catalysts, and substrates. The invention also provides compositions effective in carrying out the 1,4-hydride addition of α,β-unsaturated carbonyl compounds.

Organocatalytic transfer hydrogenation of cyclic enones

The first enantioselective organocatalytic transfer hydrogenation of cyclic enones has been accomplished. The use of iminium catalysis has provided a new organocatalytic strategy for the enantioselective reduction of β,β-substituted α,β-unsaturated cycloalkenones, to generate β-stereogenic cyclic ketones. The use of imidazolidinone 4 as the asymmetric catalyst has been found to mediate the hydrogenation of a large class of enone substrates with tert-butyl Hantzsch ester serving as an inexpensive source of hydrogen. The capacity of catalyst 4 to enable enantioselective transfer hydrogenation of cycloalkenones has been extended to five-, six-, and seven-membered ring systems. The sense of asymmetric induction is in complete accord with the stereochemical model first reported in conjunction with the use of catalyst 4 for enantioselective ketone Diels-Alder reactions. Copyright