35023-71-3

Usage

Uses

Used in Organic Synthesis:
2-Chloro-4-nitrophenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows for further chemical modifications and reactions, making it a valuable building block in the development of new molecules with potential applications in various fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Chloro-4-nitrophenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside can be used as a starting material for the development of new drugs. Its structural features can be exploited to design molecules with specific biological activities, such as antimicrobial, antiviral, or anticancer properties.
Used in Chemical Research:
2-CHLORO-4-NITROPHENYL-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE is also used in chemical research to study the reactivity of various functional groups and to understand the mechanisms of different chemical reactions. It can serve as a model compound for investigating the properties of similar molecules and their potential applications in various fields.
Used in Material Science:
In material science, 2-Chloro-4-nitrophenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside can be used to develop new materials with specific properties, such as improved stability, solubility, or biocompatibility. Its unique structure can be utilized to create novel materials with potential applications in various industries, including electronics, coatings, and adhesives.

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 
• 492-61-5 β-D-glucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 

Downstream Products

• 133-89-1 uridine diphosphate glucose 
• 1397274-90-6 (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime 
• 1397274-89-3 (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime 
• 1397274-88-2 (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-glucopyranoside 
• 1397274-87-1 (2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside 
• 1397274-86-0 (2-chloro-4-nitrophenyl) 6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside 
• 120221-14-9 (2-chloro-4-nitrophenyl)-β-D-glucopyranoside 
• 1397274-82-6 (2-chloro-4-nitrophenyl) 6'-deoxy-6'-methoxyamino-β-D-glucopyranoside 
• 122078-59-5 phenolindo-3'-chlorophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 122078-52-8 phenolindo-3'-chlorophenyl β-D-glucopyranoside 

Relevant academic research and scientific papers

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.

Facile and Versatile Chemoenzymatic Synthesis of Enterobactin Analogues and Applications in Bacterial Detection

Siderophores, such as enterobactin (Ent), are small molecules that can be selectively imported into bacteria along with iron by cognate transporters. Siderophore conjugates are thus a promising strategy for delivering functional reagents into bacteria. In this work, we present an easy-to-perform, one-pot chemoenzymatic synthesis of functionalized monoglucosylated enterobactin (MGE). When functionalized MGE is conjugated to a rhodamine fluorophore, which affords RhB-Glc-Ent, it can selectively label Gram-negative bacteria that utilize Ent, including some E. coli strains and P. aeruginosa. V. cholerae, a bacterium that utilizes linearized Ent, can also be weakly targeted. Moreover, the targeting is effective under iron-limiting but not iron-rich conditions. Our results suggest that the RhB-Glc-Ent probe is sensitive not only to the bacterial strain but also to the iron condition in the environment.

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.

Natural product disaccharide engineering through tandem glycosyltransferase catalysis reversibility and neoglycosylation

A two-step strategy for disaccharide modulation using vancomycin as a model is reported. The strategy relies upon a glycosyltransferase-catalyzed 'reverse' reaction to enable the facile attachment of an alkoxyamine-bearing sugar to the vancomycin core. Ne