96443-42-4

Basic information

• Product Name: 1,3-Cyclopentanedicarboxylicacid, 1-methyl ester, (1R,3S)-
• Synonyms: 1,3-Cyclopentanedicarboxylicacid, monomethyl ester, (1R-cis)- (9CI)
• CAS NO: 96443-42-4
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 96443-42-4.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Cyclopentanedicarboxylicacid, 1-methyl ester, (1R,3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Cyclopentanedicarboxylicacid, 1-methyl ester, (1R,3S)-(96443-42-4)
• EPA Substance Registry System: 1,3-Cyclopentanedicarboxylicacid, 1-methyl ester, (1R,3S)-(96443-42-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 96443-42-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 96443-42-4 differently. You can refer to the following data:
1. An intermediate in the stereoselective
2. An intermediate in the stereoselective synthesis of Amidinomycin.

Upstream product

• 67-56-1 methanol 
• 6054-16-6 cis-1,3-cyclopentanedicarboxylic acid anhydride 
• 498-66-8 norborn-2-ene 
• 876-05-1 cis-1,3-cyclopentanedicarboxylic acid 
• 39590-04-0 (1R,3S)-dimethyl cyclopentane-1,3-dicarboxylate 
• 124-41-4 sodium methylate 
• 6054-16-6 cyclopentane-1,3-dicarboxylic acid anhydride 

Downstream Products

• 58240-93-0 methyl cis-3-hydroxymethylcyclopentancarboxylate 
• 140210-16-8 (1R,3S)-3-Isocyanato-cyclopentanecarboxylic acid 
• 71830-07-4 (1S,3R)-3-aminocyclopentanecarboxylic acid 
• 71830-08-5 (1R,3S)-3-aminocyclopentanecarboxylic acid 
• 116891-16-8 (+/-)-1--5-methyl-2,4(1H,3H)-pyrimidinedione benzoate 
• 116891-20-4 (+/-)-1--2,4(1H,3H)-pyrimidinedione benzoate 
• 116891-18-0 (+/-)-2,3-dihydro-1--2-thioxo-4(1H)-pyrimidinone benzoate 
• 116940-94-4 Benzoic acid (1S,3R)-3-(4-chloro-5-methyl-2-oxo-2H-pyrimidin-1-yl)-cyclopentylmethyl ester 
• 116940-95-5 Benzoic acid (1S,3R)-3-(4-chloro-2-oxo-2H-pyrimidin-1-yl)-cyclopentylmethyl ester 
• 116940-85-3 (+/-)-cis-3-(hydroxymethyl)cyclopentanecarboxamide 

Relevant articles and documents

Conformational Restriction and Enantioseparation Increase Potency and Selectivity of Cyanoguanidine-Type Histamine H4 Receptor Agonists

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.

Cross-linked crystals of subtilisin: Versatile catalyst for organic synthesis

Cross-linked enzyme crystals (CLECs) of subtilisin exhibit excellent activity in aqueous and various organic solvents. This catalyst is more stable than the native enzyme in both aqueous and mixed aqueous/organic solutions. Subtilisin-CLEC was shown to be a versatile catalyst. It was used for the syntheses of peptides and peptidomimetics, mild hydrolysis of amino acid and peptide amides, enantio- and regioselective reactions, and transesterifications.

Enantioselective synthesis of (+) and (-)-cis-3-aminocyclopentanecarboxylic acids by enzymatic asymmetrization

Both enantiomers of cis-3-aminocyclopentanecarboxylic acid (GABA analogs, inhibitory neurotransmitter) have been prepared via enzymatic asymmetrization of cis -1,3-cyclopentanedicarboxylic acid.