三乙酰葡萄糖烯, Tri-O-acetyl-D-glucal

3,4,6-Tri-O-acetyl-D-glucal, also called 1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol triacetate, is the acetate protected cyclic enol-ether (glycal) of D-glucose. 3,4,6-Tri-O-acetyl-D-glucal is a building block useful in the synthesis of a range of carbohydrates with the glucal double bond allowing other functional groups to be introduced. As an alkene, a glycal can undergo electrophilic addition across the double bond to introduce halogens and epoxides or be used to generate deoxy monosaccharides. 3,4,6-Tri-O-acetyl-D-glucal can undergo a Ferrier rearrangement with an alcohol and Lewis acid to give a 2,3-unsaturated product.

Tri-O-acetyl-D-glucal is a carbohydrate derivative commonly used in organic synthesis. The compound is produced from glucose through chemical modifications, including the acetylation of hydroxyl groups. Commercially, it is also known as acetylated glucal (AG).

Synthesis and Characterization

Tri-O-acetyl-D-glucal can be synthesized through the acetylation of glucose using acetic anhydride as a reagent. The process involves the reaction of glucose with excess acetic anhydride to yield the product. The compound can be characterized using various techniques, including NMR spectroscopy, IR spectroscopy, and X-ray crystallography.

Analytical Methods

Analytical methods used to determine the purity and quality of Tri-O-acetyl-D-glucal include high-performance liquid chromatography (HPLC), thin-layer chromatography (TLC), and mass spectrometry (MS).

Biological Properties

Tri-O-acetyl-D-glucal has been shown to have antibacterial, antifungal, and antitumor activities. The compound inhibits the growth of various bacterial and fungal strains, including Escherichia coli and Candida albicans. Additionally, it has been found to inhibit the proliferation of cancer cells.

Toxicity and Safety in Scientific Experiments

There is limited information available on the toxicity and safety of Tri-O-acetyl-D-glucal in scientific experiments. However, it has been shown to be relatively safe in animals when administered at low doses.

Applications in Scientific Experiments

Tri-O-acetyl-D-glucal is used in a variety of scientific experiments, including organic synthesis, carbohydrate chemistry, and medicinal chemistry. It is commonly used as a synthetic building block in the preparation of various glycosides.

Current State of Research

Current research on Tri-O-acetyl-D-glucal focuses on its potential applications in drug discovery and development, particularly in the treatment of cancer and infectious diseases. Additionally, researchers are exploring new synthetic methods for the compound that may improve its efficiency and yield.

Potential Implications in Various Fields of Research and Industry

Tri-O-acetyl-D-glucal has potential applications in various fields of research and industry, including:

- Pharmaceuticals: Tri-O-acetyl-D-glucal can be used in the development of novel therapeutics for the treatment of cancer and infectious diseases.

- Materials Science: The compound can be used in the synthesis of various materials, including biodegradable polymers and hydrogels.

- Food Science: Tri-O-acetyl-D-glucal has potential applications in the food industry, particularly in the development of functional foods and nutraceuticals.

Limitations and Future Directions

Despite its potential applications, there are limitations associated with the use of Tri-O-acetyl-D-glucal. These limitations include:

- Limited solubility in non-polar solvents

- Low stability in acidic conditions

- Limited information on its toxicity and safety in scientific experiments

Future research directions for Tri-O-acetyl-D-glucal include:

- Development of new synthetic methods that increase efficiency and yield

- Exploration of its potential applications in drug discovery and development, materials science, and food science

- Studies on its toxicity and safety in scientific experiments to ensure its safe use in research and industry.

Product name: 3, 4, 6-Tri-O-acetyl-D-glucal                             CAS: 2873-29-2

M.F.: C₁₂H₁₆O₇      M.W._: 272.25     Batch No: 20120710       Quantity:50gfrom 55kg