79831-88-2

Usage

Uses

Used in Pharmaceutical Industry:
3,4,5-TRIS(BENZYLOXY)BENZYL ALCOHOL is used as a synthetic intermediate for the production of pharmaceutical compounds. Its unique structure allows it to be a key component in the synthesis of various drugs, contributing to the development of new medications and therapies.
Used in Chemical Research:
In the field of chemical research, 3,4,5-TRIS(BENZYLOXY)BENZYL ALCOHOL is utilized as a starting material for the synthesis of complex organic molecules. Its versatile structure makes it a valuable tool for exploring new chemical reactions and developing innovative synthetic pathways.
Used in the Synthesis of Benserazide Impurity B (A611100):
3,4,5-TRIS(BENZYLOXY)BENZYL ALCOHOL plays a crucial role in the synthesis of Benserazide Impurity B (A611100), a chemical compound of interest in pharmaceutical research. Its involvement in this synthesis process highlights its importance in the development of new drugs and the understanding of their impurities and side effects.

InChI:InChI=1/C28H26O4/c29-18-25-16-26(30-19-22-10-4-1-5-11-22)28(32-21-24-14-8-3-9-15-24)27(17-25)31-20-23-12-6-2-7-13-23/h1-17,29H,18-21H2

Upstream product

• 100-39-0 benzyl bromide 
• 79831-86-0 methyl 3-(benzyloxy)-4,5-dihydroxybenzoate 
• 100-44-7 benzyl chloride 
• 475161-97-8 benzyl 3,4,5-tris(benzyloxy)benzoate 
• 1486-48-2 3,4,5-tribenzyloxybenzoic acid 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 70424-94-1 methyl 3,4,5-tris(benzyloxy)benzoate 
• 99-24-1 methyl galloate 
• 121-79-9 Propyl gallate 

Downstream Products

• 96277-83-7 (((5-(chloromethyl)benzene-1,2,3-triyl)tris(oxy))tris(methylene))tribenzene 
• 332386-67-1 ethyl (E)-3,4,5-tris(benzyloxy)cinnamate 
• 1034402-66-8 (3,4,5-tris[benzyloxy]-2-iodophenyl)methanol 
• 1313895-26-9 C₄₃H₃₆O₄ 
• 1204316-11-9 5-(3,4,5-trihydroxyphenyl)valeric acid 
• 1131849-60-9 C₃₆H₃₂O₅ 
• 1131849-77-8 C₃₆H₃₂O₅ 
• 1131849-56-3 (-)-5,7-dideoxy-gallocatechin gallate 

Relevant academic research and scientific papers

Understanding the regioselectivity in the oxidative condensation of catechins using pyrogallol-type model compounds

Catechins are found in many foods, including tea. These compounds are bioactive. Previous studies have shown that catechins form dimers on oxidation, and there seem to be distinct regioselective effects. However, the dimerization mechanism and regioselectivity are not well understood. Therefore, we investigated the oxidation of four pyrogallol-type model compounds of epigallocatechin (EGC) having various substituents with 1 equiv of copper chloride and 30% dioxane in water. Compounds having 2C-2C or 2C-4C bonds in the B-ring were obtained in different product ratios. Comparison of the oxidation rates of each compound revealed that the model compounds having an oxygen atom corresponding to the 1-position of the C-ring of EGC underwent slow oxidation. In addition, using density functional theory calculations, we found that the highest occupied molecular orbital energies of these compounds were higher than those of the others. Further, the 2C-2C-bonded oxidation product having an A-ring and an oxygen atom at the C-ring 1-position was confirmed to have the highest thermodynamic stability. From these results, it is suggested that the regioselective condensation reaction of the catechin B-ring is related to interactions between the A-rings, as indicated by earlier studies, and the presence of oxygen at the 1-position of the C-ring in EGC.

PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED ISOXAZOLINE COMPOUNDS - CRYSTALLINE TOLUENE SOLVATE OF (S)-AFOXOLANER

This invention relates to processes for the preparation of antiparasitic isoxazoline compounds enriched in an enantiomer using quinine- based chiral phase transfer catalysts. The invention also relates to novel quinine-based phase transfer catalysts and t

POLYCATENAR LIGANDS AND HYBRID NANOPARTICLES MADE THEREFROM

Described herein are polycatenar ligand compounds and their use in the production of hybrid nanoparticles, typically nanocrystals. The present disclosure also relates to films containing the hybrid nanoparticles described herein and their use.

Polycatenar Ligand Control of the Synthesis and Self-Assembly of Colloidal Nanocrystals

Hydrophobic colloidal nanocrystals are typically synthesized and manipulated with commercially available ligands, and surface functionalization is therefore typically limited to a small number of molecules. Here, we report the use of polycatenar ligands d

π-Stacking assisted redox active peptide-gallol conjugate: Synthesis of a new generation of low-toxicity antimicrobial silver nanoparticles

In this study, we describe the rational design and synthesis of a redox-active petide-gallol conjugate and explore its application in the preparation of antimicrobial silver nanoparticles. Increase in acidity and redox activity of peptide-gallol compounds

Complex columnar hexagonal polymorphism in supramolecular assemblies of a semifluorinated electron-accepting naphthalene bisimide

Simple synthetic methods for a strongly electron-accepting naphthalene bisimide (NBI) derivative functionalized with a new environmentally friendly chiral racemic semifluorinated alkyl group and with AB3 minidendrons containing the same semifluorinated group are reported. The semifluorinated dendron was attached to the imide groups of the NBI via one, two, and three (m = 1, 2, 3) methylenic units. The NBI-containing semifluorinated groups and the dendronized NBI with m = 1 and 2 self-organize into lamellar crystals. The dendronized NBI with m = 3 self-assembles into an unprecedentedly complex and ordered column that self-organizes in a columnar hexagonal periodic array. This array undergoes a continuous transition to a columnar hexagonal superlattice that does not display a first-order phase transition during analysis by differential scanning calorimetry at heating and cooling rates of 10 and 1 °C/min. These complex columnar hexagonal periodic arrays with intramolecular order could be elucidated only by a combination of powder and fiber X-ray diffraction studies and solid-state NMR experiments. The lamellar crystals self-organized from m = 1 and the two highly ordered columnar hexagonal periodic arrays of m = 3 are assembled via thermodynamically controlled processes. Since strongly electron-accepting derivatives are of great interest to replace fullerene acceptors in organic photovoltaics and for other supramolecular electronic materials, the multitechnique structural analysis methodology elaborated here must be taken into consideration in all related studies.

Visual detection of fluoride ions

Dendrimer-hydrazides are coupled to polycyclic aromatic hydrocarbons for use in the visual detection of the presence of low levels of fluoride in a sample. The dendrimers can have a phenyl core, a first generation of aralkyl ethers, and an optional second generation of aralkyl ethers. The compounds form gels with solvents. In the presence of fluoride ion, the gels undergo color changes and/or gel to liquid phase change.

Design, synthesis and characterization of novel inhibitors against mycobacterial β-ketoacyl CoA reductase FabG4

We report the design and synthesis of triazole-polyphenol hybrid compounds 1 and 2 as inhibitors of the FabG4 (Rv0242c) enzyme of Mycobacterium tuberculosis for the first time. A major advance in this field occurred only a couple of years ago with the X-ray crystal structure of FabG4, which has helped us to design these inhibitors by the computational fragment-based drug design (FBDD) approach. Compound 1 has shown competitive inhibition with an inhibition constant (Ki) value of 3.97 ± 0.02 μM. On the other hand, compound 2 has been found to be a mixed type inhibitor with a Ki value of 0.88 ± 0.01 μM. Thermodynamic analysis using isothermal titration calorimetry (ITC) reveals that both inhibitors bind at the NADH co-factor binding domain. Their MIC values, as determined by resazurin assay against M. smegmatis, indicated their good anti-mycobacterial properties. A preliminary structure-activity relationship (SAR) study supports the design of these inhibitors. These compounds may be possible candidates as lead compounds for alternate anti-tubercular drugs. All of the reductase enzymes of the Mycobacterium family have a similar ketoacyl reductase (KAR) domain. Hence, this work may be extrapolated to find structure-based inhibitors of other reductase enzymes. The Royal Society of Chemistry.

ANTAGONISTS OF THE TOLL-LIKE RECEPTOR 1/2 COMPLEX

Provided are compounds, compositions and methods for treating Toll-like receptor 1/2 complex (TLRI/2) related inflammatory disorders. Small molecules, based on the benzotropolone scaffold, capable of influencing downstream signaling are dislcosed as well as methods of making and modifying these molecules. Also provided are methods for treating a subject for a clinical condition associated with Toll? like receptor complex 1/2 activation, comprising administering to the subject an effective amount of a benzotropolone compound.

Transformation from kinetically into thermodynamically controlled self-organization of complex helical columns with 3d periodicity assembled from dendronized perylene bisimides

The dendronized perylene 3,4:9,10-tetracarboxylic acid bisimide (PBI), (3,4,5)12G1-1-PBI, was reported by our laboratory to self-assemble into complex helical columns containing dimers of dendronized PBI with one molecule in each stratum, with different intra- and interdimer rotation angles but identical intra- and interdimer distance of 3.5 ?, exhibiting a four-strata 2 1 helical repeat. A thermodynamically controlled 2D columnar hexagonal phase with short-range intracolumnar order represents the thermodynamic product at high temperature, while a kinetically controlled monoclinic columnar array with 3D periodicity is the thermodynamic product at low temperature. With heating and cooling rates higher than 10 C/min to 1 C/min, at low temperature the 2D columnar periodic array is the kinetic product for this dendronized PBI. Here the synthesis and structural analysis of a library of (3,4,5)nG1-m-PBI with n = 12 to 6 and m = 1 are reported. A combination of differential scanning calorimetry, X-ray diffraction on powder and orientated fibers, including pattern simulation and electron density map reconstruction, and solid-state NMR, all as a function of temperature and heating and cooling rate, was employed for their structural analysis. It was discovered that at low temperature the as-prepared n = 12 to 10 exhibit a 3D layered array that transforms irreversibly into columnar periodicities during heating and cooling. Also the kinetically controlled 3D columnar phase of n = 12 becomes thermodynamically controlled for n = 10, 9, 8, 7, and 6. This unprecedented transformation is expected to facilitate the design of functions from dendronized PBI and other self-assembling building blocks.