38953-70-7

Basic information

• Product Name: 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)imidazole
• Synonyms: 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)imidazole;1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)imidazole;1-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl)-1H-imidazole;1-(2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl)imidazole
• CAS NO: 38953-70-7
• Molecular Formula: C₁₇H₂₂N₂O₉
• Molecular Weight: 398.36458
• Mol File: 38953-70-7.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)imidazole(38953-70-7)
• EPA Substance Registry System: 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)imidazole(38953-70-7)

Safety Data

• Hazardous Substances Data: 38953-70-7(Hazardous Substances Data)

Usage

Description

1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)imidazole is a synthetic chemical compound that is a derivative of β-D-glucopyranosyl and imidazole, two significant biochemical molecules. It is characterized by its unique structure, which features four acetyl groups attached to the glucose molecule and an imidazole moiety that adds functional diversity. 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)imidazole is widely utilized in chemical and biological research as a reagent or building block for the synthesis of other compounds, making it a versatile tool in the fields of chemistry and biochemistry.

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 articles and documents

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.

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.

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.