1,2,3,4,6-Penta-O-acetyl-b-D-glucopyranose

1,2,3,4,6-beta-D-葡萄糖五乙酸酯,

1,2,3,4,6-Penta-O-acetyl-b-D-glucopyranose, also known as beta-D-glucose pentaacetate, has high chemical stability and long shelf life. This protected form of glucose is a key building block of any chemical synthesis of glucose-containing oligosaccharides or glycoconjugates. In the presence of Lewis acids it can be used as a glycosyl donor to make simple glycosides. In order to perform more complex glycosylations, it can be converted into more reactive donors, such as glycosyl halides or thioglycosides. Beta-D-glucose pentaacetate is also used as a food additive and flavouring agent.

Beta-D-Glucose Pentaacetate, also known as Pentaacetyl-D-Glucopyranose, is an ester made from the reaction of acetic anhydride with D-Glucose. This compound is increasingly being investigated in scientific research due to its unique properties that make it suitable for a variety of applications. In this paper, we will examine the definition, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, the current state of research, and potential implications in various fields of research and industry.

Definition and Background

Beta-D-Glucose Pentaacetate is an ester formed through an acylation reaction between acetic anhydride and D-glucose. It is an off-white crystalline powder with a molecular formula of C16H22O11 and a molecular weight of 390.34 g/mol. This compound is a derivative of glucose and is widely used in chemical research, as a chemical reagent, and in pharmaceuticals.

Physical and Chemical Properties

Beta-D-Glucose Pentaacetate is soluble in organic solvents such as chloroform, ethyl acetate, and methanol. It has a melting point of 114 to 118 °C and a boiling point of 290 °C. It is slightly soluble in water and stable under normal temperature and pressure.

Synthesis and Characterization

The synthesis of Beta-D-Glucose Pentaacetate involves the reaction of acetic anhydride with D-glucose in the presence of a catalyst such as pyridine. The reaction results in the formation of Beta-D-Glucose Pentaacetate and acetic acid as a by-product. The product is then purified by recrystallization.

Beta-D-Glucose Pentaacetate can be characterized by various analytical methods such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry. The NMR spectrum of Beta-D-Glucose Pentaacetate shows characteristic peaks at δ 2.06, 2.17, 2.28, 2.40, and 5.30 ppm, which are attributed to the protons of the acetyl groups and the anomeric proton of glucose. The IR spectrum shows characteristic peaks at 1745, 1735, 1725, and 1655 cm−1 corresponding to the carbonyl groups of the acetyl groups.

Analytical Methods

Various analytical methods are used to measure Beta-D-Glucose Pentaacetate’s purity, identity, and concentration. These include high-performance liquid chromatography (HPLC), gas chromatography (GC), and thin-layer chromatography (TLC). HPLC is the most commonly used method for quantifying Beta-D-Glucose Pentaacetate in samples.

Biological Properties

Beta-D-Glucose Pentaacetate has been shown to exhibit antibacterial, antifungal, and antiviral properties. It has been reported to inhibit the growth of bacteria such as Staphylococcus aureus and Escherichia coli. It has also been shown to inhibit the growth of the fungus Candida albicans.

Toxicity and Safety in Scientific Experiments

According to studies conducted on rats, Beta-D-Glucose Pentaacetate shows low toxicity and does not cause any acute adverse effects. However, further research is needed to determine its long-term toxicity and safety in humans.

Applications in Scientific Experiments

Beta-D-Glucose Pentaacetate has been widely used in scientific research as a building block for synthesizing various complex pharmaceuticals, chiral compounds, and carbohydrate derivatives. It has been used as a precursor in the synthesis of antiviral drugs such as acyclovir and nucleoside analogs. It has also been used as a chirality source in the synthesis of new chiral compounds.

Current State of Research

Research on Beta-D-Glucose Pentaacetate is ongoing in various fields such as pharmaceuticals, analytical chemistry, and material science. Recent studies have focused on synthesizing new carbohydrate derivatives using Beta-D-Glucose Pentaacetate as a building block.

Potential Implications in Various Fields of Research and Industry

Beta-D-Glucose Pentaacetate has the potential to be used in various fields of research and industry. In the pharmaceutical industry, it can be used in the synthesis of new antiviral, anticancer, and antifungal drugs. In material science, it can be used in the synthesis of new chiral materials and catalytic agents. Moreover, it can be used as a chemical reagent in analytical chemistry.

Limitations and Future Directions

Despite the vast potential applications of Beta-D-Glucose Pentaacetate, there are still some limitations that need to be addressed. One of the main limitations is the lack of research on its long-term toxicity and safety in humans. Furthermore, there is a need for further research on the synthesis and characterization of new carbohydrate derivatives using Beta-D-Glucose Pentaacetate as a building block. Finally, further studies need to be conducted to determine the potential applications of Beta-D-Glucose Pentaacetate in various fields of research and industry.

Future Directions

Future research should focus on addressing the limitations of Beta-D-Glucose Pentaacetate, including its long-term toxicity and safety in humans. Furthermore, there is a need to develop new analytical methods to quantify Beta-D-Glucose Pentaacetate in complex matrices such as biological fluids. Finally, the potential applications of Beta-D-Glucose Pentaacetate need to be investigated further in fields such as material science, analytical chemistry, and pharmaceuticals.

Conclusion

Beta-D-Glucose Pentaacetate is a unique carbohydrate derivative that has gained increasing attention in scientific research due to its remarkable properties. It has been widely used as a building block for synthesizing various complex pharmaceuticals, chiral compounds, and carbohydrate derivatives. Further research is needed to determine the potential applications of Beta-D-Glucose Pentaacetate in various fields of research and industry.

COA:

Product name: Beta-D-Glucose pentaacetate;Beta-1,2,3,4,6-Pentacetyl-D-glucose            CAS: 604-69-3      

M.F.: C₁₆H₂₂O₁₁           M.W._: 390.34             Batch No: 20130913                                       Quantity: 23kg

References:

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2. Hendricks SB, Wulf OR, Liddel U, J. Am. Chem. Soc. 1936, p1997
3. Horita DA, Hajduk PJ, Lerner LE, Glycoconjugate J. 1997, 14, 5, p691