227783-08-6

Usage

Uses

Used in Pharmaceutical Industry:
(1R,3S)-1,3-Cyclohexanedicarboxylic Acid 1-Ethylester is used as a key intermediate in the synthesis of potent and selective inhibitors of Candida albicans N-myristoyltransferase. This enzyme plays a crucial role in the fungal pathogen's survival and virulence, making it a promising target for the development of new antifungal agents. The compound's unique stereochemistry and functional groups contribute to its effectiveness in this application, potentially leading to the creation of novel therapeutics for the treatment of Candida-related infections.

Upstream product

• 62059-56-7 cis-1,3-Cyclohexanedicarboxylic acid diethyl ester 
• 2305-30-8 (1R)-cyclohexane-1,3-dicarboxylic acid 
• 4355-31-1 3-oxabicyclo<3.3.1>nonane-2,4-dione 

Downstream Products

• 851075-68-8 ethyl (1R,3S)-3-[(tert-butoxycarbonyl)amino]cyclohexanecarboxylate 
• 53084-60-9 ethyl 3-aminocyclohexanecarboxylate 
• 1259278-09-5 ethyl (1R,3S)-3-benzyloxycarbonylaminocyclohexane-1-carboxylate 
• 952616-39-6 (1R,3S)-3-(((benzyloxy)carbonyl)amino)cyclohexanecarboxylic acid 
• 1259278-11-9 benzyl N-[(1S,3R)-3-carbamoylcyclohexyl]carbamate 
• 1259278-12-0 benzyl N-[(1S,3R)-3-aminocyclohexyl]carbamate 
• 1259279-66-7 benzyl (1S,3R)-3-(4-chlorobutanamido)cyclohexylcarbamate 
• 1259366-99-8 ethyl (1R,3S)-3-((2-chloro-5-fluoropyrimidin-4-yl)amino)cyclohexane-1-carboxylate 
• 1383485-55-9 (1R,3S)-ethyl 3-(3,5-difluoro-6-(5-fluoro-1-trityl-1H-pyrazolo[3,4-b]pyridin-3-yl)pyridin-2-ylamino)cyclohexanecarboxylate 
• 1383485-56-0 (1R,3S)-3-(3,5-difluoro-6-(5-fluoro-1-trityl-1H-pyrazolo[3,4-b]pyridin-3-yl)pyridin-2-ylamino)cyclohexanecarboxylic acid 
• 1383485-77-5 (1R,3S)-3-(3,5-difluoro-6-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)pyridin-2-ylamino)cyclohexanecarboxylic acid 
• 1383485-54-8 (1R,3S)-ethyl 3-(6-bromo-3,5-difluoropyridin-2-ylamino)cyclohexanecarboxylate 
• 1259279-62-3 N-[(1R,3S)-3-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]-pyridin-3-yl)pyrimidin-4-yl]amino]cyclohexyl]morpholine-4-carboxamide 
• 1259279-59-8 tert-butyl N-[(1R,3S)-3-[[5-fluoro-2-[5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]amino]cyclohexyl]carbamate 

Relevant academic research and scientific papers

Development of a Scalable Synthesis of an Azaindolyl-Pyrimidine Inhibitor of Influenza Virus Replication

A scalable, asymmetric route for the synthesis of the influenza virus replication inhibitor 2 is presented. The key steps include an enzymatic desymmetrization of cis-1,3-cyclohexanediester in 99% yield and 96% ee, SNAr displacement of a methanesulfinylpyrimidine, and a Curtius rearrangement to form a morpholinyl urea. This high-yielding route allowed us to rapidly synthesize hundreds of grams of 2 in 99% purity to support in vivo studies.

Synthesis of potent and selective inhibitors of Candida albicans N-myristoyltransferase based on the benzothiazole structure

Two parallel synthetic methods using solid-supported reagents were established to examine the rapid optimization of weak hit compound 1. Several compounds showed high potency in the low nanomolar range against N-myristoyltransferase. The structure-activity relationship (SAR) and antifungal activities of a series of novel 2-aminobenzothiazole N-myristoyltransferase inhibitors are presented.

Stereoselective process for preparing cylcohexyl amine derivatives

A process for preparing (1R,3S)-3-(9-chloro-3-methyl-4-oxo-5H-(isoxazoloquinolin-5-yl))cyclohexanecarboxylic acid and esters thereof, as represented by formulas II and III, wherein R is a lower alkyl groups, and A and B are N or O, provided that when A is N, B is O, or when A is O, B is N: Formula (III) and Formula (II).

STEREOSELECTIVE PROCESS FOR PREPARING CYCLOHEXYL AMINE DERIVATIVES

A process for preparing (1R,3S)-3-(9-chloro-3-methyl-4-oxo-5H-(isoxazoloquinolin-5-yl))cyclohexanecarboxylic acid and esters thereof, as represented by formulas II and III, wherein R is a lower alkyl groups, and A and B are N or O, provided that when A is

Enzymatic desymmetrization of cis-1,3-cyclohexanedicarboxylic acid diesters

cis-1,3-Cyclohexanedicarboxylic acid (1,3-CHDA) monoesters were prepared in high overall yield and high enantiomeric purity using a three step process from cis/trans-1,3-CHDA. The asymmetry is induced by an enzymatic hydrolytic desymmetrization of a meso