2872-66-4

Basic information

• Product Name: 1-(4-NITROPHENYL)-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE
• Synonyms: 1-(4-NITROPHENYL)-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE;P-NITROPHENYL-BETA-D-GALACTOPYRANOSIDE TETRAACETATE;Nsc89591
• CAS NO: 2872-66-4
• Molecular Formula: C₂₀H₂₃NO₁₂
• Molecular Weight: 469.3961
• Product Categories: Carbohydrates & Derivatives
• Mol File: 2872-66-4.mol
• Article Data: 35

Chemical Properties

• Melting Point: 144-145 °C
• Boiling Point: 559.3°Cat760mmHg
• Flash Point: 207.1°C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 1.53E-12mmHg at 25°C
• Refractive Index: 1.54
• Solubility: Chloroform
• CAS DataBase Reference: 1-(4-NITROPHENYL)-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-NITROPHENYL)-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE(2872-66-4)
• EPA Substance Registry System: 1-(4-NITROPHENYL)-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE(2872-66-4)

Safety Data

• Hazardous Substances Data: 2872-66-4(Hazardous Substances Data)

Usage

Description

1-(4-NITROPHENYL)-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE, also known as p-Nitrophenyl 2,3,4,6-Tetra-O-acetyl-β-D-galactopyranoside, is a yellow oil compound with the chemical formula C26H29NO15. It is a derivative of β-D-galactopyranoside, a monosaccharide, with four acetyl groups attached to the 2, 3, 4, and 6 positions and a 4-nitrophenyl group at the 1 position. 1-(4-NITROPHENYL)-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE is useful in organic synthesis and has potential applications in various industries.

Uses

Used in Organic Synthesis:
1-(4-NITROPHENYL)-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows for selective reactions and modifications, making it a valuable building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
1-(4-NITROPHENYL)-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE is used as a key component in the development of pharmaceutical compounds. Its ability to form stable derivatives and its reactivity make it suitable for the synthesis of drug candidates with potential therapeutic applications.
Used in Chemical Research:
1-(4-NITROPHENYL)-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE is used as a research tool in chemical laboratories. Its unique properties and reactivity enable scientists to study various chemical reactions and mechanisms, contributing to the advancement of chemical knowledge and the development of new synthetic methods.
Used in Analytical Chemistry:
1-(4-NITROPHENYL)-2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSIDE is used as a reference compound in analytical chemistry. Its distinct chemical properties and spectral characteristics make it suitable for calibration and validation of analytical instruments and methods, ensuring accurate and reliable measurements in various applications.

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

• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-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 
• 100-02-7 4-nitro-phenol 
• 108-24-7 acetic anhydride 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 572-09-8 acetobromogalactose 
• 86520-63-0 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 25878-60-8 D-galactose pentaacetate 
• 824-78-2 4-nitrophenol sodium salt 
• 1420786-80-6 C₂₉H₂₈O₁₁ 
• 4163-60-4 β-D-galactose peracetate 

Downstream Products

• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 170940-41-7 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acetylamino-phenoxy)-tetrahydro-pyran-3-yl ester 
• 42011-36-9 (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-aminophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 249512-66-1 Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-methyleneamino-phenoxy)-tetrahydro-pyran-4-yl ester 
• 249512-63-8 Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-formylamino-phenoxy)-tetrahydro-pyran-4-yl ester 
• 4163-60-4 β-D-galactose peracetate 
• 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 articles and documents

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.

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.