153823-58-6

Basic information

• Product Name: 2-CHLORO-4-NITROPHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE
• Synonyms: 2-Chloro-4-nitrophenyl 2,3,4,6-tetrα-O-acetyl-α-D-glucopyranoside;2-Chloro-4-nitrophenyl α-D-Glucopyranoside 2,3,4,6-Tetraacetate;2-Chloro-4-Nitrophenyl alpha-D-Glucopyranoside 2,3,4,6-Tetraacetate
• CAS NO: 153823-58-6
• Molecular Formula: C20H22ClNO12
• Molecular Weight: 503.84
• EINECS: 1533716-785-6
• Product Categories: Carbohydrates & Derivatives
• Mol File: 153823-58-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 117-119°C
• Boiling Point: 574.3±50.0 °C(Predicted)
• Appearance: /
• Density: 1.44±0.1 g/cm3(Predicted)
• Refractive Index: 1.55
• CAS DataBase Reference: 2-CHLORO-4-NITROPHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-4-NITROPHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE(153823-58-6)
• EPA Substance Registry System: 2-CHLORO-4-NITROPHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE(153823-58-6)

Safety Data

• Hazardous Substances Data: 153823-58-6(Hazardous Substances Data)

Usage

Description

2-Chloro-4-nitrophenyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside, with the CAS number 153823-58-6, is a white solid compound that plays a significant role in organic synthesis. It is a derivative of glucopyranoside, a monosaccharide commonly found in various biological systems, and is characterized by its unique chemical structure that includes a chloro and nitro group attached to a phenyl ring.

Uses

Used in Organic Synthesis:
2-Chloro-4-nitrophenyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside is used as an intermediate in organic synthesis for the production of various complex organic compounds. Its unique structure allows for a wide range of chemical reactions, making it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Chloro-4-nitrophenyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside is used as a key component in the development of novel drug candidates. Its ability to participate in various chemical reactions enables the creation of new molecules with potential therapeutic properties, contributing to the advancement of drug discovery and development.
Used in Research and Development:
2-Chloro-4-nitrophenyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside is also utilized in research and development settings, where it serves as a valuable tool for studying the properties and reactivity of complex organic molecules. Its unique structure and functional groups make it an ideal candidate for investigating various chemical reactions and mechanisms, furthering our understanding of organic chemistry and its applications.

InChI:InChI=1/C20H22ClNO12/c1-9(23)29-8-16-17(30-10(2)24)18(31-11(3)25)19(32-12(4)26)20(34-16)33-15-6-5-13(22(27)28)7-14(15)21/h5-7,16-20H,8H2,1-4H3/t16?,17-,18+,19+,20+/m1/s1

Upstream product

• 619-08-9 2-chloro-4-nitrophenol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 83-87-4 D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 492-61-5 β-D-glucose 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 83-87-4 penta-O-acetyl-α-D-galactopyranose 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 604-68-2 α-D-glucopyranose peracetylate 

Downstream Products

• 1397274-82-6 (2-chloro-4-nitrophenyl) 6'-deoxy-6'-methoxyamino-β-D-glucopyranoside 
• 1397274-86-0 (2-chloro-4-nitrophenyl) 6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside 
• 1397274-87-1 (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside 
• 1397274-88-2 (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-glucopyranoside 
• 1397274-89-3 (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime 
• 1397274-90-6 (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime 
• 119047-14-2 2-chloro-4-nitrophenyl α-D-glucopyranoside 
• 119047-14-2 2-chloro-4-nitrophenyl α-D-galactopyranoside 

Relevant articles and documents

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

An Efficient Strategy for the Chemo-Enzymatic Synthesis of Bufalin Glycosides with Improved Water Solubility and Inhibition against Na+, K+-ATPase

In this study, bufalin was glycosylated by an efficient chemo-enzymatic strategy. Firstly, 2-chloro-4-nitrophenyl-1-O-β-D-glucoside (sugar donors) was obtained by chemical synthesis. Then, the glycosylation of the bufalin was achieved with the synthesized sugar donor under the catalysis of two glycosyltransferases (Loki and ASP). Finally, two glycosides, i. e., bufalin-3-O-β-D-glucopyranoside and bufalin-3-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside)], were obtained by preparative HPLC. Compared to our previously reported sole chemical (total yield 10 % in four steps) or enzymatic methods (30 %), our combined chemo-enzymatic strategy in this article greatly improves the yields of monoglycoside (68 %) and diglycoside (21 %) and decreased the experimental cost (90 %). Furthermore, we tested the water solubility of these glycosides and found that the water solubilities of the two glycosides were 13.1 and 53.7 times of bufalin, respectively. In addition, the inhibitory activity of these glycosides against Na+, K+-ATPase were evaluated. The mono-glycosylated compound showed more potent activity than bufalin, while the diglycosylated compound was less potent.

Binuclear copper(II) complexes discriminating epimeric glycosides and α- And β-glycosidic bonds in aqueous solution

Two chiral binuclear copper(II) complexes were synthesized and characterized for the first time as efficient chemoselective catalysts for the hydrolysis of aryl glycosides and disaccharides in aqueous solution at near neutral pH. Under these conditions, discrimination of epimeric aryl α-glycopyranosides was observed by both 29-fold different reaction rates and 3-fold different proficiency of the catalyst. Additionally, large differentiation of the nature of α- and β-glycosidic bond in aryl glycosides as model compounds is apparent, but also noted in selected disaccharides. The influence of the chirality of the complexes and the role of the configuration of the carbohydrate upon interaction with the catalyst is discussed in detail. Lastly, a putative mechanism for the metal complex-catalyzed hydrolysis is derived from the experimental evidence pointing at deprotonation of the hydroxyl group at C-2 as a pre-requisite for glycoside hydrolysis.