17042-32-9

Usage

Uses

Used in Biochemical Research:
2,4-dinitrophenyl 2,3,4,6-tetra-O-acetylhexopyranoside is used as a reagent for detecting the presence of carbohydrates in various samples. Its sensitivity to sugars, such as glucose and fructose, makes it a valuable tool in carbohydrate analysis and research.
Used in Carbohydrate Detection:
In the field of biochemical research, 2,4-dinitrophenyl 2,3,4,6-tetra-O-acetylhexopyranoside is used as a detection agent for identifying the presence of carbohydrates. Its ability to react with carbohydrates and form a colored product aids in the identification and analysis of sugar content in different samples.
Used in Laboratory Experiments:
2,4-dinitrophenyl 2,3,4,6-tetra-O-acetylhexopyranoside is employed in laboratory experiments as a detection tool for carbohydrates. Its reactivity with sugars allows researchers to observe and analyze the presence of specific sugars in their samples, contributing to the understanding of carbohydrate chemistry and its applications.

Upstream product

• 51-28-5 2,4-Dinitrophenol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranose 
• 896-80-0 1-benzenesulfonyl-2,4-dinitro-benzene 
• 25775-97-7 2,4-dinitrophenyl β-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 604-69-3 β-D-glucose pentaacetate 
• 2280-44-6 D-Glucose 

Downstream Products

• 77516-86-0 1-O-(2,4-dinitrophenyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 25775-97-7 2,4-dinitrophenyl β-D-glucopyranoside 

Relevant academic research and scientific papers

The role of sugar substituents in glycoside hydrolysis

A series of monosubstituted deoxy and deoxyfluoro 2,4-dinitrophenyl (DNP) β-D-glycopyranosides was synthesized and used to probe the mechanism of spontaneous β-glycoside hydrolysis. Their relative rates of hydrolysis followed the order 2-deoxy > 4-deoxy > 3-deoxy ? 6-deoxy > parent > 6-deoxy- 6-fluoro > 3-deoxy-3-fluoro > 4-deoxy-4-fluoro > 2-deoxy-2-fluoro. Hammett correlations of the pH-independent hydrolysis rates of each of the 6-, 4-, 3- , and 2-position substituted glycosides with the σ1 value for the sugar ring substituent were linear (r = 0.95 to 0.999, π(I) = -2.2 to -10.7), consistent with hydrolysis rates being largely dictated by field effects on an electron-deficient transition state. The relative rates of hydrolysis of the DNP glucosides can be rationalized on the basis of the stabilities of the oxocarbenium ion-like transition states, as predicted by the Kirkwood- Westheimer model. The primary determinant of the rate of hydrolysis within a series appears to be the field effect of the ring substituent on O5, the principal center of charge development at the transition state. Differences in the rates of hydrolysis between different series of hexopyranosides may not arise solely from field effects and likely also reflect differences in steric factors or solvation.

Direct anomeric O-arylation and O-hetarylation of glucose electron deficient aromatic and hetaromatic compounds in aryl and hetaryl glycoside synthesis

Anomeric O-arylation and O-hctarylation of tetra-O-bcnzyl-, tetra-O-acctyl-, and O-unprotected glucose (1a-c) can be directly performed with electron dcficienl aromatic and hctcroaromatic systems having fluoro- (2A-2F) or phenylsulfonyl (3B, 3G-3K), respectively, as leaving groups. The reactions were carried out in DMF as solvent at room temperature with NaH as the base; they led in the products 4 to an exchange of the leaving group by the glucopyranosyloxy moicly; mainly β-products were obtained.

Silver Imidazolate-assisted Glycosidations. Part 7. Synthesis of 1,2-trans-Linked Aryl Glycosides

Efficient preparations of 1,2-trans-linked aryl glycosides starting from fully acetylated glycopyranosyl bromides are described.The promoting system is silver imidazolate and zink chloride.

The use of the 2,4-dinitrophenyl group in sugar chemistry re-examined

The use of the tertiary base 1,4-diazabicyclooctane, together with 1-fluoro-2,4-dinitrobenzene in the solvent DMF, proved to be an efficient method for the introduction of the 2,4-dinitrophenyl (DNP) group at different positions, including the anom