156469-00-0

Basic information

• Product Name: (2R)-3-cyclohexyl-2-hydroxypropionic acid
• Synonyms: (2R)-3-cyclohexyl-2-hydroxypropionic acid
• CAS NO: 156469-00-0
• Molecular Weight: 172.224
• Mol File: 156469-00-0.mol

Chemical Properties

• CAS DataBase Reference: (2R)-3-cyclohexyl-2-hydroxypropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-3-cyclohexyl-2-hydroxypropionic acid(156469-00-0)
• EPA Substance Registry System: (2R)-3-cyclohexyl-2-hydroxypropionic acid(156469-00-0)

Safety Data

• Hazardous Substances Data: 156469-00-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2R)-3-cyclohexyl-2-hydroxypropionic acid is used as a key intermediate in the synthesis of various pharmaceuticals and fine chemicals. Its chiral nature allows for the production of enantiomerically pure compounds, which are essential for the development of effective and safe medications.
Used in Asymmetric Catalysis:
(2R)-3-cyclohexyl-2-hydroxypropionic acid is utilized as a chiral ligand or catalyst in asymmetric catalysis, enabling the selective formation of enantiomerically pure products. This is crucial for the synthesis of biologically active compounds and the development of enantioselective processes in the chemical industry.
Used in Neurological Disorders Treatment:
(2R)-3-cyclohexyl-2-hydroxypropionic acid has been investigated for its potential therapeutic properties in the treatment of neurological disorders. Its ability to modulate specific biological pathways and target receptors makes it a promising candidate for the development of novel treatments for various neurological conditions.
Used as an Anti-Inflammatory Agent:
(2R)-3-cyclohexyl-2-hydroxypropionic acid has also been studied for its potential as an anti-inflammatory agent. Its ability to reduce inflammation and modulate immune responses may contribute to the development of new therapies for inflammatory diseases and conditions.

Upstream product

• 27527-05-5 L-cyclohexylalanine 
• 151899-07-9 D-cyclohexylalanine hydrochloride 
• 828-01-3 phenyllactic acid 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 103-26-4 methyl cinnamate 
• 103-41-3 benzy cinnamate 
• 122743-18-4 methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate 
• 27000-00-6 methyl 2-hydroxy-3-phenylpropionate 
• 128659-92-7 (R)-methyl 2-hydroxy-3-cyclohexylpropanoate 
• 673-06-3 D-(R)-phenylalanine 
• 122-78-1 phenylacetaldehyde 
• 50353-47-4 phenyl acetaldehyde cyanohydrin 
• 62377-41-7 (S)-3-cyclohexyl-2-hydroxypropionic acid 
• 58717-02-5 3-cyclohexyl-D-alanine 

Downstream Products

• 128659-92-7 (R)-methyl 2-hydroxy-3-cyclohexylpropanoate 
• 161313-44-6 (2R)-2-(4-nitrophenyl)sulfonyloxy-3-cyclohexyl-propionic acid benzyl ester 
• 252896-26-7 2-{2-[2-benzyloxymethyl-3-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-3-cyclohexyl-propionic acid benzyl ester 
• 1053626-88-2 (S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-((R)-3-cyclohexyl-2-hydroxy-propionylamino)-pentanoic acid trityl-amide 
• 161313-45-7 (2R)-2-hydroxy-3-cyclohexyl-propionic acid benzyl ester 

Relevant articles and documents

HETEROARYLS AMIDE DERIVATIVES AND THEIR USE AS GLUCOKINASE ACTIVATORS

The present invention provides Formula (1A) compounds that act as glucokinase activators; pharmaceutical compositions thereof; and methods of treating diseases, disorders, or conditions mediated by glucokinase. X, Y, Z, R1, R2, R3, and R4 are as described herein.

Biocatalytic racemization of aliphatic, arylaliphatic, and aromatic α-hydroxycarboxylic acids

Biocatalytic racemization of a range of aliphatic, (aryl)aliphatic, and aromatic α-hydroxycarboxylic acids was accomplished by using whole resting cells of a range of Lactobacillus spp. The mild (physiological) reaction conditions ensured an essentially "clean" isomerization in the absence of side reactions, such as elimination or decomposition. Whereas straight-chain aliphatic 2-hydroxy-carboxylic acids were racemized with excellent rates (up to 85% relative to lactate), steric hindrance was observed for branched-chain analogues. Good rates were observed for aryl-alkyl derivatives, such as 3-phenyllactic acid (up to 59%) and 4-phenyl-2-hydroxybutanoic acid (up to 47%). In addition, also mandelate and its o-chloro analogue were accepted at a fair rate (45%). This biocatalytic racemization represents an important tool for the deracemization of a number of pharmaceutically important building blocks.

Biocatalytic racemisation of α-hydroxycarboxylic acids at physiological conditions

Biocatalytic racemisation of aliphatic, aryl-aliphatic and aromatic α-hydroxycarboxylic acids was accomplished using whole resting cells of Lactobacillus paracasei DSM 20207; the mild (physiological) reaction conditions ensured an essentially 'clean' isomerization in the absence of side reactions, such as elimination or decomposition. The Royal Society of Chemistry 2005.

GLYCOMIMETIC ANTAGONISTS FOR BOTH E- AND P-SELECTINGS

Compounds and methods are provided for modulating in vivo and in vivo processes mediated by selectin biniding. More specifically, selectin modulators and their use are described, wherein the selectin modulators that modulate (e.g. inhibit or enhance) a selectin-mediated function comprise particular glycomimetics linked to a member of a class of compounds termed BASAs (Benzyl Amino Sulfonic Acids).

Process research of (R)-cyclohexyl lactic acid and related building blocks: A comparative study

(S)-Cyclohexyl lactic acid is a component of the selective E-selectin inhibitor 2 ((S)-cHexLact-2-0-(3-Galβ(1→3)ddGlc-(4→1)αFuc). We describe the evaluation of various synthetic routes to this building block: (A) diazotation of phenylalanine followed by phenyl ring hydrogenation; (B) phenyl ring hydrogenation of phenyl alanine followed by diazotation; (C) acidic hydrolysis of the cyanohydrin derived from phenylacetaldehyde, enantiomeric resolution of the resulting, racemic phenyl lactic acid via diasteromeric salt formation and phenyl ring hydrogenation; (D) enantioselective dihydroxylation of a cinnamate ester, followed by hydrogenation of the benzylic hydroxy group and the aromatic nucleus; (E) enantioselective biocatalytic reduction of phenylpyruvic acid, followed by phenyl ring hydrogenation. The development of (2R)-2-0-(4-nitrophenyl)sulfonyl-cyclohexyl lactic acid p-bromobenzylester 21 as a buidling block with improved crystallinity and stability is also described.

AMINO ACID DERIVATIVES

There is provided amino acid derivatives of formula I, wherein p, q, R 1, R 2, R 3, R 4, Y, n and B have meanings given in the description which are useful as competitive inhibitors of trypsin-like proteases, such as thrombin, and in particular in the treatment of conditions where inhibition of thrombin is required (e.g. thrombosis) or as anticoagulants.

2,3-methano-amino acid compounds

Compound of formula (I): wherein: n represents 2 or 3, R1represents optionally substituted alkyl, cycloalkyl or optionally substituted phenyl, R2represents amino, optionally substituted amidino, optionally substituted guanidino or optionally substituted isothioureido, Ar represents aryl or heteroaryl, X1represents hydroxy or optionally substituted amino, isomers thereof, and also salts thereof with a pharmaceutically acceptable acid or base, and which medicinal products containing the same/are useful as trypsin-related serine protease inhibitors.

Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis

Compounds of the formula: where the formula variables are as defined herein, are disclosed that advantageously inhibit or block the biological activity of the picornaviral 3C protease. Also disclosed are compounds of the formula: where the formula variables are as defined herein that advantageously inhibit or block the biological activity of the picornaviral 3C protease. These compounds, as well as pharmaceutical compositions containing these compounds, are useful for treating patients or hosts infected with one or more picornaviruses, such as rhinovirus 3C proteases. Intermediates and synthetic methods for preparing such compounds are also described.

Synthesis and Biological Evaluation of a Potent E-Selectin Antagonist

An early step of the inflammatory response - the rolling of leukocytes on activated endothelial cells - is mediated by selectin/carbohydrate interactions. The tetrasaccharide sialyl Lewisx (sLex) 1 is a ligand for E-, P-, and L-selectin and, therefore, serves as a lead structure to develop analogues which allow the control of acute and chronic inflammation. Here we describe the efficient synthesis (10 linear steps) of the potent sLex mimetic 2. Compared to sLex, compound 2 showed a 30-fold improved affinity in a static, cell-free E-selectin-ligand binding assay (IC50 = 36 μM). These data were confirmed by a marked inhibition in an in vitro cell-cell rolling assay which simulates in vivo conditions (IC50 ca. 40 μM). The assays are predictive for the in vivo efficacy of test compounds as indicated by a marked inhibitory effect of 2 in a thioglycollate induced peritonitis model of acute inflammation in mice (ED50 ca. 15 mg/kg).