14131-42-1

Basic information

• Product Name: (4-NITRO)PHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE
• Synonyms: (4-NITRO)PHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE;P-NITROPHENYL 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE;4-Nitrophenyl2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside;4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside;4-Nitrophenyl tetra-O-acetyl-alpha-D-glucopyranoside;4-Nitrophenyl alpha-D-Glucopyranoside 2,3,4,6-Tetraacetate
• CAS NO: 14131-42-1
• Molecular Formula: C₂₀H₂₃NO₁₂
• Molecular Weight: 469.4
• EINECS: 1533716-785-6
• Product Categories: Carbohydrates & Derivatives
• Mol File: 14131-42-1.mol
• Article Data: 45

Chemical Properties

• Melting Point: 110-114°C
• Boiling Point: 559.3±50.0 °C(Predicted)
• Appearance: /
• Density: 1.38±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (4-NITRO)PHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (4-NITRO)PHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE(14131-42-1)
• EPA Substance Registry System: (4-NITRO)PHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE(14131-42-1)

Safety Data

• Hazardous Substances Data: 14131-42-1(Hazardous Substances Data)

Usage

Description

(4-NITRO)PHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE, also known as p-Nitrophenyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (CAS# 14131-42-1), is an off-white crystalline solid compound that plays a significant role in organic synthesis. It is a derivative of glucopyranoside, a type of sugar molecule, with a nitrophenyl group and four acetyl groups attached to it.

Uses

Used in Organic Synthesis:
(4-NITRO)PHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE is used as an intermediate compound in organic synthesis for the production of various complex organic molecules. Its unique structure allows it to be a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (4-NITRO)PHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE is used as a key component in the development of new drugs. Its ability to form complex structures makes it a valuable asset in the design and synthesis of novel therapeutic agents.
Used in Research and Development:
(4-NITRO)PHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE is also utilized in research and development laboratories for studying the properties and reactivity of various organic compounds. Its unique structure and functional groups make it an ideal candidate for exploring new reaction pathways and understanding the underlying mechanisms of organic reactions.
Used in Material Science:
In the field of material science, (4-NITRO)PHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE can be employed as a component in the development of advanced materials with specific properties, such as improved stability, enhanced reactivity, or tailored physical characteristics.
Overall, (4-NITRO)PHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE is a versatile compound with a wide range of applications across various industries, including pharmaceuticals, organic synthesis, research and development, and material science. Its unique structure and properties make it a valuable asset in the development of new products and technologies.

Upstream product

• 100-02-7 4-nitro-phenol 
• 604-69-3 β-D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 3767-28-0 4-nitrophenyl-α-D-glucopyranoside 
• 78942-85-5 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-β-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 108-24-7 acetic anhydride 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 3947-62-4 2,3,4,6-tetraacetylglucose 
• 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 

Downstream Products

• 3767-28-0 4-nitrophenyl-α-D-glucopyranoside 
• 59862-97-4 p-aminophenyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 78530-04-8 O-p-acetanilide tetra O-acetyl-2,3,4,6 α-D-glucopyrannose 
• 217447-64-8 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(4-methyleneamino-phenoxy)-tetrahydro-pyran-4-yl ester 
• 217447-62-6 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(4-formylamino-phenoxy)-tetrahydro-pyran-4-yl ester 
• 554434-74-1 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(4-azido-butyrylamino)-phenoxy]-tetrahydro-pyran-3-yl ester 
• 554434-75-2 acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-(4-{4-[(4'-{3-[4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenylcarbamoyl]-propylcarbamoyl}-[2,2']bipyridinyl-4-carbonyl)-amino]-butyrylamino}-phenoxy)-tetrahydro-pyran-3-yl ester 
• 3947-62-4 2,3,4,6-tetraacetylglucose 
• 153741-98-1 4-Methyl-N-[4-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-benzenesulfonamide 
• 153741-97-0 4-Nitro-N-[4-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-benzenesulfonamide 
• 925695-06-3 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[4-(toluene-4-sulfonylamino)-phenoxy]-tetrahydro-pyran-4-yl ester 
• 925694-99-1 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(4-nitro-benzenesulfonylamino)-phenoxy]-tetrahydro-pyran-3-yl ester 
• 1303982-23-1 C₃₄H₄₀N₄O₁₀ 

Relevant articles and documents

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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.

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.