1098881-13-0 Usage
Description
(1R,3S)-3-(methoxycarbonyl)cyclopentane-1-carboxylic acid is a chiral organic compound that features a cyclopentane ring with a carboxylic acid and a methoxycarbonyl group attached. It possesses a specific stereochemistry characterized by a 1R and 3S configuration, which is crucial for its potential applications in various fields.
Uses
Used in Organic Synthesis:
(1R,3S)-3-(methoxycarbonyl)cyclopentane-1-carboxylic acid is utilized as a key intermediate in organic synthesis for the creation of complex organic molecules. Its unique structure and stereochemistry make it a valuable building block for the development of novel compounds with specific properties.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (1R,3S)-3-(methoxycarbonyl)cyclopentane-1-carboxylic acid serves as a vital component in drug discovery and development. Its stereochemistry plays a significant role in the biological activity of the resulting compounds, making it an essential tool for studying the effects of stereochemistry on drug efficacy and safety.
Used in the Development of New Drugs:
(1R,3S)-3-(methoxycarbonyl)cyclopentane-1-carboxylic acid is employed as a starting material or a structural element in the design and synthesis of new pharmaceutical agents. Its unique properties and reactivity contribute to the creation of innovative drugs with improved therapeutic potential.
Used in the Study of Stereochemical Effects on Biological Activity:
(1R,3S)-3-(methoxycarbonyl)cyclopentane-1-carboxylic acid is also used in research aimed at understanding the impact of stereochemistry on the biological activity of molecules. This knowledge is crucial for optimizing drug design and ensuring that the desired therapeutic effects are achieved with minimal side effects.
Used in the Synthesis of Natural Products:
Due to its structural features, (1R,3S)-3-(methoxycarbonyl)cyclopentane-1-carboxylic acid may have potential applications in the synthesis of natural products and other complex organic molecules. Its ability to be modified and incorporated into larger structures makes it a useful component in the development of bioactive natural product analogs.
Check Digit Verification of cas no
The CAS Registry Mumber 1098881-13-0 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,0,9,8,8,8 and 1 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1098881-13:
(9*1)+(8*0)+(7*9)+(6*8)+(5*8)+(4*8)+(3*1)+(2*1)+(1*3)=200
200 % 10 = 0
So 1098881-13-0 is a valid CAS Registry Number.
1098881-13-0Relevant articles and documents
Chemoenzymatic Enantioselective Synthesis of Amidinomycin
Chenevert, Robert,Lavoie, Michele,Courchesne, Gabriel,Martin, Richard
, p. 93 - 96 (1994)
We report the first asymmetric synthesis of amidinomycin, an antiviral antibiotic metabolite.Amidinomycin of high enantiomeric purity (ee 91percent) was prepared from norbornylene in 8 steps.The key step is an enzymatic discrimination of enantiotopic groups in meso cis-1,3-dicarbomethoxycyclopentane or in meso cis-cyclopentane-1,3-dicarboxylic acid anhydride.
Conformational Restriction and Enantioseparation Increase Potency and Selectivity of Cyanoguanidine-Type Histamine H4 Receptor Agonists
Geyer, Roland,Nordemann, Uwe,Strasser, Andrea,Wittmann, Hans-Joachim,Buschauer, Armin
supporting information, p. 3452 - 3470 (2016/05/19)
2-Cyano-1-[4-(1H-imidazol-4-yl)butyl]-3-[2-(phenylsulfanyl)ethyl]guanidine (UR-PI376, 1) is a potent and selective agonist of the human histamine H4 receptor (hH4R). To gain information on the active conformation, we synthesized analogues of 1 with a cyclopentane-1,3-diyl linker. Affinities and functional activities were determined at recombinant hHxR (x: 1-4) subtypes on Sf9 cell membranes (radioligand binding, [35S]GTPγS, or GTPase assays) and in part in luciferase assays on human or mouse H4R (HEK-293 cells). The most potent H4R agonists among 14 racemates were separated by chiral HPLC, yielding eight enantiomerically pure compounds. Configurations were assigned based on X-ray structures of intermediates and a stereocontrolled synthetic pathway. (+)-2-Cyano-1-{[trans-(1S,3S)-3-(1H-imidazol-4-yl)cyclopentyl]methyl}-3-[2-(phenylsulfanyl)ethyl]guanidine ((1S,3S)-UR-RG98, 39a) was the most potent H4R agonist in this series (EC50 11 nM; H4R vs H3R, >100-fold selectivity; H1R, H2R, negligible activities), whereas the optical antipode proved to be an H4R antagonist ([35S]GTPγS assay). MD simulations confirmed differential stabilization of the active and inactive H4R state by the enantiomers.
Highly enantioselective desymmetrizations of meso-anhydrides
Schmitt, Ellen,Schiffers, Ingo,Bolm, Carsten
experimental part, p. 6349 - 6357 (2010/10/03)
Readily available, low molecular cyclohexane-based organocatalysts promote highly enantioselective desymmetrizations of cyclic meso-anhydrides applying alcohols and benzyl mercaptan as nucleophiles. Both succinic and glutaric anhydrides furnished the corresponding products with up to 96% ee in mostly quantitative yields.
