53585-93-6

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(-)-Hexahydromandelic acid is used as an intermediate in the synthesis of antimycobacterial compound pyridomycin analogs. These analogs are essential in the development of new drugs to combat tuberculosis and other mycobacterial infections, which are significant global health concerns.
Used in Analytical Chemistry:
(R)-(-)-Hexahydromandelic acid serves as a model α-hydroxy acid compound in the chirality sensing studies of organic probes using the circular dichroism technique. This application is vital for understanding the interactions between chiral molecules and their environment, which is crucial in the development of new chiral drugs and materials.
Used in Chemical Synthesis:
(R)-(-)-Hexahydromandelic acid is used as a starting material in the synthesis of chiral ionic liquids. These chiral ionic liquids are applicable as chiral solvents in asymmetric synthesis, which is a critical process in the production of enantiomerically pure compounds. Additionally, they can be used as chiral stationary phases in chromatographic separations, enabling the efficient and selective separation of enantiomers in various applications, such as pharmaceuticals, agrochemicals, and environmental analysis.

Purification Methods

It forms hexagonal clusters on recrystallisation from CCl4 or Et2O. [Wood & Comley J Chem Soc 2638 1924, Lettré et al. Chem Ber 69 1594 1936]. The racemate has m 137.2-137.6o (134-135o) [Smith et al. J Am Chem Soc 71 3772 1949]. [Beilstein R-10 II 5; S-10 II 6.]

InChI:InChI=1/C8H14O3/c9-7(8(10)11)6-4-2-1-3-5-6/h6-7,9H,1-5H2,(H,10,11)/t7-/m1/s1

Upstream product

• 4354-47-6 (R)-2-cyclohexyl-2-hydroxyacetonitrile 
• 106975-25-1 ethyl (R)-2-hydroxy-2-cyclohexylacetate 
• 157982-33-7 (R)-S-ethylthio cyclohexylglycolate 
• 172288-96-9 (R)-Cyclohexyl-hydroxy-acetaldehyde 
• 62455-70-3 3-cyclohexyl-3-oxopropanenitrile 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 4354-49-8 2-cyclohexyl-2-oxoethanoic acid 
• 108-85-0 1-bromocyclohexane 
• 69455-34-1 rac-2-cyclohexenyl-2-hydroxyethanoic acid 
• 17392-16-4 (2-hydroxyphenyl)oxoacetic acid 
• 42607-71-6 2-(cyclohex-2-enyl)-2-hydroxyethanoic acid 
• 134970-42-6 2-chloro-1-cyclohexyl-2-propen-1-ol 
• 57741-12-5 α-(trichloromethyl)cyclohexanemethanol 
• 37166-70-4 acetic acid 2-cyclohexyl-2-oxoethyl ester 

Downstream Products

• 92587-21-8 Methyl (R)-α-hydroxycyclohexaneacetate 
• 106975-25-1 ethyl (R)-2-hydroxy-2-cyclohexylacetate 
• 512785-95-4 (R)-1-cyclohexyl-1-hydroxy-butan-2-one 
• 82919-05-9 (R)-2-Cyclohexyl-1-cyclopropyl-2-hydroxy-ethanone 
• 174603-02-2 benzyl (R)-2-cyclohexyl-2-hydroxyacetate 
• 439117-46-1 [4-Chloro-2-({[(S)-1-((R)-2-cyclohexyl-2-hydroxy-acetyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-benzyl]-carbamic acid tert-butyl ester 
• 123054-48-8 2-(4-Isobutyl-phenyl)-propionic acid (R)-cyclohexyl-methoxycarbonyl-methyl ester 
• 1207474-70-1 (R)-2-cyclohexyl-2-(nitrooxy)acetic acid 
• 1450833-17-6 C₁₈H₃₄N₂O₆ 

Relevant academic research and scientific papers

Selective Monovalent Galectin-8 Ligands Based on 3-Lactoylgalactoside

Galectin-8 has gained attention as a potential new pharmacological target for the treatment of various diseases, including cancer, inflammation, and disorders associated with bone mass reduction. To that end, new molecular probes are needed in order to better understand its role and its functions. Herein we aimed to improve the affinity and target selectivity of a recently published galectin-8 ligand, 3-O-[1-carboxyethyl]-β-d-galactopyranoside, by introducing modifications at positions 1 and 3 of the galactose. Affinity data measured by fluorescence polarization show that the most potent compound reached a KD of 12 μM. Furthermore, reasonable selectivity versus other galectins was achieved, making the highlighted compound a promising lead for the development of new selective and potent ligands for galectin-8 as molecular probes to examine the protein's role in cell-based and in vivo studies.

Readily Accessible 1,2-Amino Ether Ligands for Enantioselective Intramolecular Carbolithiation

A new class of chiral 1,2-amino ether ligands, readily accessible from naturally occurring α-amino- or α-hydroxy acids, was found to provide high levels of both conversion and stereocontrol (up to 95:5 er) in intramolecular carbolithiation reactions, outperforming the benchmark ligand (?)-sparteine. The ligand could be used in a substoichiometric amount (0.25 equiv) without significant loss of enantioselectivity.

Asymmetric hydrogenation reaction of alpha-ketoacids compound

The invention relates to the technical field of organic chemistry, especially to an asymmetric hydrogenation reaction of an alpha-ketoacids compound. The asymmetric hydrogenation reaction comprises a scheme shown in the description. In the scheme, R1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, C1-C6 alkyl, or aralkyl; a substituent group is C1-C6 alkyl, C1-C6 alkoxy, or halogen; and the number of the substituent group is 1-3. In the scheme, M is a chiral spiro-pyridylamino phosphine ligand iridium complex having a structure shown in the description. In the structure, R is hydrogen, 3-methyl, 4-tBu, or 6-methyl.

Chemo- And stereoselective reduction of β-keto-α-oximino nitriles by using baker's yeast

The baker's yeast mediated reduction of β-keto-α-oximino nitriles 3 at 20 ° C gave β-hydroxy-α-oximino nitriles 4 in high yields with high enantiomeric purity [enantiomeric excess (ee) values >99%]. At room temperature, the same reaction afforded the product in a slightly lower yield. The β-hydroxy-α-oximino nitriles 4 were obtained as single stereoisomers according to chiral GC-MS analyses and the 1H and 19F NMR spectra of the corresponding Mosher esters. The abso-lute stereochemistry of alcohol 4a was determined by hydrolysis of its oximino nitrile group followed by conversion into its corresponding α-hydroxy ester. The β-hydroxy-α-oximino nitrile products were further submitted to oxime- and nitrileselective transformations. This chemo- and stereoselective reduction can be used to generate important chiral building blocks.

Carboxylation with CO2 via brook rearrangement: Preparation of α-hydroxy acid derivatives

In the presence of CsF, a wide range of α-substituted α-siloxy silanes were carboxylated under a CO2 atmosphere (1 atm) via Brook rearrangement. A variety of α-substituents including aryl, alkenyl, and alkyl groups were tolerated to afford α-hydroxy acids in moderate-to-high yields. One-pot synthesis from aldehydes using PhMe2SiLi and CO 2 was also possible, providing α-hydroxy acids without the isolation of an α-hydroxy silane.

Direct asymmetric hydrogenation of α-keto acids by using the highly efficient chiral spiro iridium catalysts

A new efficient and highly enantioselective direct asymmetric hydrogenation of α-keto acids employing the Ir/SpiroPAP catalyst under mild reaction conditions has been developed. This method might be feasible for the preparation of a series of chiral α-hydroxy acids on a large scale.

SOLUBLE EPOXIDE HYDROLASE INHIBITORS

Disclosed are alpha keto amide and alpha hydroxy amide compounds and compositions that inhibit soluble epoxide hydrolase (sEH), methods for preparing the compounds and compositions, and methods for treating patients with such compounds and compositions. The compounds, compositions, and methods are useful for treating a variety of sEH mediated diseases, including hypertensive, cardiovascular, inflammatory, pulmonary, and diabetic-related diseases.

An efficient new synthesis of racemic cetiedil and a novel route to α-ketocarboxylic acids utilising mild conditions

We describe a new efficient synthesis of the prescribed racemic drug cetiedil [(±)-2-cyclohexyl-2-(3-thienyl)ethanoic acid 2-(hexahydro-1H-azepin-1-yl)ethylester], Additionally, we report herein a high yielding large scale, route to its acid precursor 7, subsequently enabling large-scale synthesis of the chiral forms of cetiedil, and detailed pharmacological investigations. Additionally, we describe a novel route to α-ketocarboxylic acids, starting from readily available or easily obtainable aldehydes: The mild conditions utilised opens up its applicability for use on molecules of biological interest. Georg Thieme Verlag Stuttgart.

Cyclic alkyl substituted glycolides and polylactides therefrom

Cyclic alkyl, particularly cyclohexyl, substituted glycolides and polylactides are described. The polylactides have a high glass transition temperature and improved clarity.

Lithiated camphor-derived oxazolidinone S,N-acetals as chiral formyl anion synthons in additions to aldehydes. Asymmetric synthesis of α-hydroxy aldehydes and α-hydroxy acids

N-(Phenylthiomethyl)oxazolidinones derived from camphor can be lithiated and added to aldehydes in good yields and stereoselectivities. The adducts are crystalline, which simplifies isolation of the major diastereomer from the product mixture. Hydrolysis affords enantiopure α-hydroxy aldehydes, which can be oxidized to α-hydroxy acids in good yields. The steric course of the reaction is analyzed in detail and a mechanistic model is presented.