5709-98-8Relevant articles and documents
Kinetic Resolution of Nearly Symmetric 3-Cyclohexene-1-carboxylate Esters Using a Bacterial Carboxylesterase Identified by Genome Mining
Dou, Zhe,Chen, Xuanzao,Niwayama, Satomi,Xu, Guochao,Ni, Ye
supporting information, p. 3043 - 3047 (2021/05/05)
A new bacterial carboxylesterase (CarEst3) was identified by genome mining and found to efficiently hydrolyze racemic methyl 3-cyclohexene-1-carboxylate (rac-CHCM) with a nearly symmetric structure for the synthesis of (S)-CHCM. CarEst3 displayed a high substrate tolerance and a stable catalytic performance. The enantioselective hydrolysis of 4.0 M (560 g·L-1) rac-CHCM was accomplished, yielding (S)-CHCM with a >99% ee, a substrate to catalyst ratio of 1400 g·g-1, and a space-time yield of 538 g·L-1·d-1.
Asymmetric Synthesis of Optically Active 3-Cyclohexene-1-carboxylic Acid Utilizing Lactic Ester as a Chiral Auxiliary in the Diastereoselective Diels–Alder Reaction
Fujita, Ryunosuke,Hayashi, Wakana,Kubota, Shunichi,Nishi, Tatsuya,Nishiyama, Akira,Ochiai, Hidenori,Sasagawa, Miwa
supporting information, (2022/02/09)
The optically active 3-cyclohexene-1-carboxylic acid was synthesized through a TiCl4-catalyzed diastereoselective Diels–Alder reaction utilizing lactic acid ester as a chiral auxiliary, which can be removed by washing with H2O. The (S)- and (R)-isomers were both derived from easily available ethyl l-lactate.
Preparation method of edoxaban tosylate and isomers thereof
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Paragraph 0122-0124-0128, (2021/02/06)
The invention discloses a preparation method of edoxaban tosylate and isomers thereof. By taking a compound (I) and a compound (II) as starting materials, the method can be used to prepare any one ofhigh-purity edoxaban tosylate (1S, 2R, 4S), edoxaban tosylate enantiomers (1R, 2S, 4R), edoxaban tosylate epimers (1R, 2R, 4S) and edoxaban tosylate epimers (1S, 2S, 4R). Effective guarantee is provided for process research and quality control of the edoxaban tosylate bulk drug and related preparations, the preparation method is suitable for commercialization, the produced edoxaban tosylate bulk drug is high in purity and has great significance and practical value, and the production of the edoxaban tosylate bulk drug and the control of drug quality are facilitated.
Preparation method of (R)-3-cyclohexeneformic acid
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Paragraph 0018-0027, (2021/04/14)
The invention discloses a preparation method of (R)-3-cyclohexenecarboxylic acid, and belongs to the technical field of medical intermediates. The preparation method comprises the following steps: refluxing 3-cyclohexenecarboxylic acid and 0.5 eq(1S, 2S)-
An efficient stereoselective synthesis of six stereoisomers of 3, 4-diaminocyclohexane carboxamide as key intermediates for the synthesis of factor Xa inhibitors
Wang, Xin,Ma, Mingliang,Reddy, Alavala Gopi Krishna,Hu, Wenhao
, p. 1381 - 1388 (2017/02/18)
An efficient stereoselective route for the preparation of six stereoisomers of tert-butyl ((1R, 2S, 5S)-2-amino-5-(dimethylcarbamoyl)cyclohexyl)carbamate 1 starting from simple 3-cyclohexene-1-carboxylic acid has been described. Stereochemistry of the tit
OPTICAL RESOLUTION METHOD FOR CARBOXYLIC ACID
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Paragraph 0042, (2017/03/08)
PROBLEM TO BE SOLVED: To provide a method for optical resolution of carboxylic acid. SOLUTION: Provided is a method for optical resolution of carboxylic acid in which (S)-3-cyclohexene-1-carboxylic acid represented by the chemical structure of the left side in formula (II) is produced from 3-cyclohexene-1-carboxylic acid represented by formula (I) by using, as solvent, hydrous acetonitrile and/or hydrous 2-propanol, and, as optical resolution agent, (1R,2S)-1-amino-2-indanol represented by the chemical structure of the right side in Formula (II). SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
GLYCOMIMETIC-PEPTIDOMIMETIC INHIBITORS OF E-SELECTINS AND CXCR4 CHEMOKINE RECEPTORS
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, (2012/05/20)
Compounds, compositions and methods are provided for treating cancer and inflammatory diseases, and for releasing cells such as stem cells (e.g., bone marrow progenitor cells) into circulating blood and enhancing retention of the cells in the blood. More specifically, glycomimetic-peptidomimetic compounds that inhibit both E-selectins and CXCR4 chemokine receptors are described.
Pre-organization of the core structure of E-selectin antagonists
Schwizer, Daniel,Patton, John T.,Cutting, Brian,Smiesko, Martin,Wagner, Beatrice,Kato, Ako,Weckerle, Celine,Binder, Florian P. C.,Rabbani, Said,Schwardt, Oliver,Magnani, John L.,Ernst, Beat
, p. 1342 - 1351 (2012/04/04)
A new class of N-acetyl-dglucosamine (GlcNAc) mimics for Eselectin antagonists was designed and synthesized. The mimic consists of a cyclohexane ring substituted with alkyl substituents adjacent to the linking position of the fucose moiety. Incorporation into E-selectin antagonists led to the test compounds 8 and the 2'-benzoylated analogues 21, which exhibit affinities in the low micromolar range. By using saturation transfer difference (STD)-NMR it could be shown that the increase in affinity does not result from an additional hydrophobic contact of the alkyl substituent with the target protein E-selectin, but rather from a steric effect stabilizing the antagonist in its bioactive conformation. The loss of affinity found for antagonists 10 and 35 containing a methyl substituent in a remote position (and therefore unable to support to the stabilization of the core) further supports this hypothesis. Finally, when a GlcNAc mimetic containing two methyl substituents (52 and 53) was used, in which one methyl was positioned adjacent to the fucose linking position and the other was in a remote position, the affinity was regained.
Enantioselective synthesis of oseltamivir phosphate
Raghavan, Sadagopan,Babu, Vaddela Sudheer
experimental part, p. 2044 - 2050 (2011/04/17)
The key steps in the enantioselective synthesis of Tamiflu include an asymmetric Diels-Alder reaction, Mitsunobu inversion using Fukuyama modified Weinreb reagent, carbamate directed epoxidation. Epoxide opening with trimethylsilyl azide furnished a 3:1 mixture of regioisomers that converged to afford the same aziridine. Attempted preparation of the unsaturated ester regioselectively using 2-iodoxybenzoic acid (IBX) following Nicolaou's protocol failed. The unsaturated ester was prepared by phenylselenylation followed by selenoxide elimination.
Enantiomerically pure amines
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, (2011/12/12)
A compound of formula wherein PROT, PROT' and R have various meanings, processes for its production and production of intermediates in stereoisomerically pure form, and its use for the production of pharmaceutically active compounds.