187404-16-6

Basic information

• Product Name: benzyl (R)-3-cyclohexyl-2-trifluoromethanesulfonyloxy-propionate
• Synonyms: benzyl (R)-3-cyclohexyl-2-trifluoromethanesulfonyloxy-propionate
• CAS NO: 187404-16-6
• Molecular Weight: 394.412
• Mol File: 187404-16-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: benzyl (R)-3-cyclohexyl-2-trifluoromethanesulfonyloxy-propionate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl (R)-3-cyclohexyl-2-trifluoromethanesulfonyloxy-propionate(187404-16-6)
• EPA Substance Registry System: benzyl (R)-3-cyclohexyl-2-trifluoromethanesulfonyloxy-propionate(187404-16-6)

Safety Data

• Hazardous Substances Data: 187404-16-6(Hazardous Substances Data)

Upstream product

• 828-01-3 D-phenyllactic acid 
• 50353-47-4 phenyl acetaldehyde cyanohydrin 
• 122-78-1 phenylacetaldehyde 
• 673-06-3 D-(R)-phenylalanine 
• 100-39-0 benzyl bromide 
• 128659-92-7 (R)-methyl 2-hydroxy-3-cyclohexylpropanoate 
• 27000-00-6 methyl 2-hydroxy-3-phenylpropionate 
• 122743-18-4 methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate 
• 103-41-3 benzy cinnamate 
• 103-26-4 methyl cinnamate 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 828-01-3 phenyllactic acid 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 161313-45-7 (2R)-2-hydroxy-3-cyclohexyl-propionic acid benzyl ester 

Downstream Products

• 1374760-28-7 C₇₀H₈₃NO₁₇ 
• 322761-81-9 ethyl 3-O-[(1S)-1-(cyclohexylmethyl)-2-oxo-2-(phenylmethoxy)ethyl]-1-thio-β-D-galactopyranoside 2,4,6-tribenzoate 
• 645411-60-5 C₅₅H₇₀O₁₅ 

Relevant articles and documents

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.

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).

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).