38953-70-7

Usage

Uses

Used in Chemical Research:
1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)imidazole is used as a reagent in chemical research for its ability to participate in various chemical reactions and modifications due to its unique structure with four acetyl groups attached to the glucose molecule.
Used in Biological Research:
In biological research, 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)imidazole is used as a building block for the synthesis of other compounds, taking advantage of the functional diversity provided by the imidazole moiety, which allows for potential interactions with biological systems.
Used in Pharmaceutical Industry:
1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)imidazole is used as an intermediate in the pharmaceutical industry for the development of new drugs, leveraging its structural properties to create novel therapeutic agents.
Used in Material Science:
In the field of material science, 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)imidazole is used as a component in the design and synthesis of advanced materials, such as polymers and nanoparticles, that can have applications in various industries, including healthcare, electronics, and environmental management.

Upstream product

• 288-32-4 1H-imidazole 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 

Downstream Products

• 35786-40-4 1-β-D-glucopyranosylimidazole 

Relevant academic research and scientific papers

Allyl palladium complexes bearing carbohydrate-based N-heterocyclic carbenes: Anticancer agents for selective and potent in vitro cytotoxicity

Novel allyl palladium compounds stabilized by carbohydrate-based N-heterocyclic carbenes (NHCs) were prepared and characterized by nuclear magnetic resonance, high-resolution mass spectrometry and elemental analysis. The antiproliferative activity of the compounds was tested on a panel of different tumor lines, especially ovarian cancer and MRC-5 human lung fibroblasts (nontumor cells). These experiments showed that both mixed NHC/PPh3 and NHC/PTA (PTA = 1,3,5-triaza-7-phosphaadamantane) allyl complexes have IC50 (half maximal inhibitory concentration) values comparable and sometimes even significantly lower than cisplatin. Moreover, the mixed NHC/PTA allyl complexes exhibit good activity toward the seven tumor lines tested with a substantial inactivity against normal cells, a necessary condition to avoid the general cytotoxicity of a metallo-drug. Furthermore, this subclass of compounds proved particularly active on the A549 lung cancer tumor line (up to 100-fold more cytotoxic than cisplatin) and exhibited satisfactory cytotoxicity against KURAMOCHI and OVCAR3 cell lines, which are currently considered the best in vitro models for serous ovarian cancer, the most lethal tumor for women worldwide.

Poly(ethylene glycol)- and glucopyranoside-substituted N-heterocyclic carbene precursors for the synthesis of arylfluorene derivatives using efficient palladium-catalyzed aqueous Suzuki reaction

This paper reports an environmentally friendly and highly efficient synthesis of organic semiconductor materials via a Pd/N-heterocyclic carbene (NHC)-catalyzed Suzuki reaction in aqueous ethanol with high isolated yields (86–98%). Firstly, four glucopyra

Synthesis of chiral imidazolium salts from a carbohydrate and their application in Pd-catalyzed Suzuki-Miyaura reaction

A series of chiral 1-(acetylated glucopyranosyl)-3-substituted-imidazolium salts [3-substitute = nbutyl (1a), 3-bromopropyl (1b), 2-chloromethyl benzyl (1c), and 4-chloromethyl benzyl (1d)] have been synthesized. Preliminary catalytic studies show that these imidazolinium salts are remarkably efficient in Pd-catalyzed Suzuki-Miyaura reaction. Functionalized aryl boronic acids reaction with aryl halides (including aryl iodides, aryl bromides and activated aryl chlorides) using environmentally friendly conditions (ethanol aqueous and ambient). The excellent isolate yields reveal that the bulky carbohydrate unit is promising for the construction of highly active transition-metal catalyst.

Unprecedented diastereoselective generation of chiral-at-metal, half sandwich Ir(iii) and Rh(iii) complexes via anomeric isomerism on "sugar-coated" N-heterocyclic carbene ligands

The first example of the diastereoselective synthesis induced by anomeric isomerism of sugar units in ligands of metal complexes was demonstrated. S and R configurations of chiral-at-metal Ir(iii) and Rh(iii) complexes were selectively obtained by using chelate-type NHC ligands with α- and β-glucopyranosyl units, respectively.

Proton-acceptor properties and capability for mutarotation of some glucosylamines in methanol

N-(m-Nitrophenyl)-β-D-glucopyranosylamine (Gln), N-(N-methylphenyl)- β-D-glucopyranosylamine (Glm), N-β-D-glucopyranosylpyrazole (Glp), and N-β-D-glucopyranosylimidazole (Gli) have been synthesized. Their basicity constants, pKb, determined in methanol were, respectively, 14.99, 14.36, 15.04, and 9.74. The derivatives of secondary amines (Glm, Glp, and Gli) did not mutarotate in methanol in the presence of 3,5-dinitrobenzoic acid and hydrochloric acid. The heats of formation and entropies were calculated by the AM1 and PM3 methods for the glucosylamines and their cations under consideration of two plausible protonation centers. Thermodynamic parameters for the proton transfer in the reaction: glucosylamine+CH3OH2 +=glucosylamineH++CH3OH were determined and the protonation center in the glucosylamine molecule was identified. The mechanism of mutarotation of the glucosylamines is discussed and the conclusion made that formation of an acyclic immonium cation is not a satisfactory condition for the reaction to proceed.

Absence of reverse anomeric effect in glycosylimidazoles

The so-called reverse anomeric effect is the preference of cationic substituents for the equatorial position on a pyranose ring, but it is not consistent with theories of molecular structure. To reinvestigate this, we have measured the N-protonation-induc