207975-84-6

Basic information

• Product Name: 2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside 3,4,6-Triacetate
• Synonyms: 2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside 3,4,6-Triacetate;2,4-Dinitrophenyl 2-deoxy-2-fluoro-β-D-galactopyranoside 3,4,6-Triacetate
• CAS NO: 207975-84-6
• Molecular Formula: C₁₈H₁₉FN₂O₁₂
• Molecular Weight: 474.3480632
• Product Categories: Aromatics;Carbohydrates & Derivatives;Aromatics, Carbohydrates & Derivatives
• Mol File: 207975-84-6.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: 2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside 3,4,6-Triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside 3,4,6-Triacetate(207975-84-6)
• EPA Substance Registry System: 2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside 3,4,6-Triacetate(207975-84-6)

Safety Data

• Hazardous Substances Data: 207975-84-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside 3,4,6-Triacetate is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows it to be a versatile building block in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
In the field of research and development, 2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside 3,4,6-Triacetate serves as a valuable tool for studying the properties and reactivity of complex carbohydrates and their derivatives. It can be used to investigate the interactions between carbohydrates and other biomolecules, as well as to develop new methods for carbohydrate synthesis and modification.
Used in Analytical Chemistry:
2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside 3,4,6-Triacetate can also be employed as a reagent in analytical chemistry for the detection and quantification of specific compounds. Its distinctive chemical properties make it suitable for use in assays and other analytical techniques that require selective and sensitive detection.

Upstream product

• 1011-73-0 sodium 2,4-dinitrophenoxide 
• 4098-06-0 triacetyl-D-galactal 
• 93253-40-8 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-galactopyranosyl bromide 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 108794-37-2 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-D-galactopyranoside 
• 75414-44-7 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-galactopyranosyl fluoride 

Downstream Products

• 143716-62-5 2,4-dinitrophenyl-2-fluoro-2-deoxy-β-D-galactopyranoside 

Relevant articles and documents

A novel direct route to 2-deoxy-2-fluoro-aldoses and their corresponding derivatives

A new type of reactive N-(2-deoxy-2-fluoro-glycosyl) compound is formed by regioselective syn-addition of the electrophilic N-F reagent Selectfluor(TM) to glycals. By subsequent treatment with nucleophiles, 2- deoxy-2-fluoro-aldoses and various C-1-substituted derivatives thereof are easily accessible. Furthermore, the reaction with D-galactal and D-arabinal proceeds stereoselectively, thus allowing the synthesis of 2-deoxy-2-fluoro- D-galactose- and -D-arabinose-derivatives in multi-gram quantities.

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.