5987-78-0

Usage

Uses

Used in Organic Synthesis:
4'-NITROPHENYL TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE is used as an intermediate compound for the synthesis of various organic molecules. Its application is due to its unique structure, which allows for further chemical reactions and modifications to create a wide range of products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4'-NITROPHENYL TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE is used as a building block for the development of new drugs. Its application is based on its ability to be modified and incorporated into complex molecular structures, potentially leading to the discovery of novel therapeutic agents.
Used in Chemical Research:
4'-NITROPHENYL TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE is also used as a research tool in chemical laboratories. Its application is due to its unique properties, which can provide insights into the behavior of similar compounds and contribute to the advancement of chemical knowledge.
Used in Material Science:
In the field of material science, 4'-NITROPHENYL TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE may be used as a component in the development of new materials with specific properties. Its application is based on its potential to be incorporated into polymers or other materials, leading to the creation of novel materials with unique characteristics.

InChI:InChI=1/C20H23NO12/c1-10(22)28-9-16-17(29-11(2)23)18(30-12(3)24)19(31-13(4)25)20(33-16)32-15-7-5-14(6-8-15)21(26)27/h5-8,16-20H,9H2,1-4H3/t16-,17-,18+,19-,20-/m1/s1

Upstream product

• 100-02-7 4-nitro-phenol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 2492-87-7 4-nitrophenyl-β-D-glucoside 
• 78942-85-5 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-β-D-glucopyranose 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 24067-17-2 4-nitrophenylboronic acid 
• 10257-28-0 D-Galactose 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 

Downstream Products

• 362660-94-4 4-Retinamidophenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 1092479-40-7 1-O-(4-nitrophenyl)-2,3,6-tri-O-acetyl-β-D-glucopyranose 
• 55101-65-0 1-O-(4-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranose 
• 1427462-39-2 5-(-N-(p-O-(2,3,4,6-tetra-O-acetyl-β-D-glucosyl)phenyl)aminocarbonyl)-2,2'-bipyridine 
• 1427462-43-8 5-(-N-(p-O-(β-D-glucosyl)phenyl)-aminocarbonyl)-2,2'-bipyridine 
• 2492-87-7 4-nitrophenyl-β-D-glucoside 
• 17042-39-6 p-nitrophenyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 
• 1427462-40-5 5-(-N-(p-O-(2,3,4,6-tetra-O-acetyl-β-D-galactosyl)phenyl)-aminocarbonyl)-2,2'-bipyridine 
• 1427462-44-9 5-(-N-(p-O-(β-D-galactosyl)phenyl)-aminocarbonyl)-2,2'-bipyridine 
• 5094-33-7 p-aminophenyl β-D-galactopyranoside 

Relevant academic research and scientific papers

p-Nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

The crystal structure of p-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside, C20H23NO12, was determined in order to ascertain its stereochemistry. The ring adopts a 3C5 chair conformation, with

Nitrogen-containing aromatic ring derivative containing galactose and application thereof

The invention belongs to the technical field of medicines, and relates to a nitrogen-containing aromatic ring derivative containing galactose, application thereof and a pharmaceutical composition containing the compound. The invention also relates to a method for preparing the compound and the pharmaceutical composition, and application of the compound and the pharmaceutical composition in prevention or treatment of tumors, inflammatory diseases, autoimmune diseases and other diseases, especially tumors.

Glucose-containing nitrogen-containing aromatic ring derivative and application thereof

The invention belongs to the technical field of medicines, and relates to a glucose-containing nitrogen-containing aromatic ring derivative and application thereof, and a pharmaceutical composition containing the compound. The invention also relates to a

Copper-mediated O-arylation of lactols with aryl boronic acids

An efficient and novel methodology to access phenolic glycosides has been established by using copper-mediated coupling reaction of aryl boronic acids with hemiacetals. The reaction takes place normally in the presence of Cu(OAc)2 (1.0 equiv.) and pyridine (2.0 equiv.) at 40 °C. This protocol distinguishes itself by wide substrate scope, operational simplicity and giving rise to a myriad of phenolic glycosides in good to excellent yields.

Chemo-enzymatic synthesis of p-nitrophenyl β-D-galactofuranosyl disaccharides from Aspergillus sp. fungal-type galactomannan

β-D-Galactofuranose (Galf) is a component of polysaccharides and glycoconjugates. There are few reports about the involvement of galactofuranosyltransferases and galactofuranosidases (Galf-ases) in the synthesis and degradation of galactofuranose-containing glycans. The cell walls of filamentous fungi in the genus Aspergillus include galactofuranose-containing polysaccharides and glycoconjugates, such as O-glycans, N-glycans, and fungal-type galactomannan, which are important for cell wall integrity. In this study, we investigated the synthesis of p-nitrophenyl β-D-galactofuranoside and its disaccharides by chemo-enzymatic methods including use of galactosidase. The key step was selective removal of the concomitant pyranoside by enzymatic hydrolysis to purify p-nitrophenyl β-D-galactofuranoside, a promising substrate for β-D-galactofuranosidase from Streptomyces species.

Beta-galactosidase-responsive synthetic biomarker for targeted tumor detection

Tumor biomarkers are highly desirable for the screening of patients with a risk of tumor development and progression. Here, we report a beta-galactosidase (β-gal)-responsive acetaminophen (β-GR-APAP) as a synthetic plasma biomarker for targeted tumor detection. Tumor β-gal labeling via the recognition of tumor-related antigen enabled the detection of a tumor using β-GR-APAP.

Development of Pseudomonas aeruginosa Lectin LecA Inhibitor by using Bivalent Galactosides Supported on Polyproline Peptide Scaffolds

LecA is a galactose-binding tetrameric lectin from Pseudomonas aeruginosa involved in infection and biofilm formation. The emergent antibiotic resistance of P. aeruginosa has made LecA a promising pharmaceutical target to treat such infections. To develop LecA inhibitors, we exploit the unique helical structure of polyproline peptides to create a scaffold that controls the galactoside positions to fit their binding sites on LecA. With a modular scaffold design, both the galactoside ligands and the inter-ligand distance can be altered conveniently. We prepared scaffolds with spacings of 9, 18, 27, and 36 ? for ligand conjugation and found that glycopeptides with galactosides ligands three helical turns (27 ?) apart best fit LecA. In addition, we tested different galactose derivatives on the selected scaffold (27 ?) to improve the binding avidity to LecA. The results validate a new multivalent scaffold design and provide useful information for LecA inhibitor development.

Diazepinium perchlorate: a neutral catalyst for mild, solvent-free acetylation of carbohydrates and other substances

Diazepinium perchlorate, an essentially neutral organic salt possessing excellent stability, has been found to be well suited for the acetylation of free as well as partially protected sugars, phenols, thiophenols, thiols and other alcohols as well as amines. The diazepinium perchlorate-catalyzed acetylation is mild, organic and solvent-free and leaves acid sensitive protecting groups such as TBDMS/TBDPS/Tr ethers and isopropylidene/benzylidene acetals present on a substrate unaffected. Regioselective hydroxyl protection in partially protected carbohydrate derivatives/polyhydroxylic compounds was possible and was proved to be a convenient time-saving alternative to the conventional synthesis of such compounds. Easy preparation of the catalyst, mild reaction conditions and an environmentally benign protocol are some of the notable features of this reaction. The results obtained on the acetylation of phenols and thiophenols could be rationalized through their local nucleophilicity index obtained from DFT calculations.

Glucose fatty acid-containing derivative preparation method and application of derivative in medical field

The invention relates to a novel p-fatty alkyl amidophenyl-beta-D-glucoside compound and a preparation method and an application thereof, which belong to the technical field of medicine. According to the invention, a structural general formula is shown as

Glycosylated lanthanide cyclen complexes as luminescent probes for monitoring glycosidase enzyme activity

The development of synthetic chemical probes for the detection of enzymes is extremely important for biological, medicinal, and industrial applications. Here we report the synthesis of an array of novel glycosylated Tb(iii) complexes, their photophysical properties in solution, and their ability to function as luminescent probes for observing glycosidase enzyme activity in real time. Our initial studies into the application of these complexes for the detection of the Concanavalin A (ConA) lectin is also reported, highlighting the broad scope of these novel chemical probes.