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14125-75-8 , 2,3,4,6-Tetra-O-benzoyl-2-hydroxy-D-glucal, CAS:14125-75-8

14125-75-8 , 2,3,4,6-Tetra-O-benzoyl-2-hydroxy-D-glucal,
CAS:14125-75-8
C34H26O9 / 578.56
MFCD00010693

2,3,4,6-Tetra-O-benzoyl-2-hydroxy-D-glucal,

2,3,4,6-四苯甲酰基-2-羟基-D-葡萄糖烯,

[(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate, also known as TBMDP, is a chemical compound with potential applications in various fields of research and industry. In this paper, we will discuss TBMDP’s definition, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions.

Definition and Background

[(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate is a complex organic molecule with the molecular formula C41H32O9. It is a benzoyl-protected derivative of the naturally occurring dihydrofurano lignan justicidin B. [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate is a pyran derivative and has been identified as a potent tubulin polymerization inhibitor. It has shown activity against various types of cancer cells, including ovarian cancer, breast cancer, and prostate cancer.

Synthesis and Characterization

[(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate can be synthesized through a four-step process that involves the protection of the dihydrofuran ring, esterification, benzoylation, and debenzylation. The first step involves the protection of the dihydrofuran ring by reacting with benzyl, followed by esterification with benzoic acid. The second step involves benzoylation of the dihydropyran ring. The final step is the debenzylation of [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate, yielding the final product. [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate can be characterized through various analytical techniques such as nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry.

Analytical Methods

[(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate can be analyzed using various analytical methods such as high-performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS). These techniques can be used to determine the purity, identity, and concentration of [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate.

Biological Properties

[(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate has shown a potential for inhibiting tubulin polymerization, which is essential for cell proliferation and division. It has also shown activity against various types of cancer cells, including ovarian cancer, breast cancer, and prostate cancer. [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate has also shown antimicrobial activity against various pathogens such as Staphylococcus aureus and Candida albicans, making it a potential candidate for the development of new antimicrobial agents.

Toxicity and Safety in Scientific Experiments

[(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate has shown low toxicity in scientific experiments, both in vitro and in vivo. Studies have shown that [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate does not disrupt the normal cell cycle or induce apoptosis in normal cells. However, further studies are needed to determine the long-term effects of [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate exposure.

Applications in Scientific Experiments

[(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate has potential applications in various fields of research, including cancer research, drug discovery, and antimicrobial research. It can be used as a lead compound for the development of new anticancer and antimicrobial agents.

Current State of Research

Research on [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate is still at an early stage, with only a few studies investigating its potential applications in cancer and antimicrobial research. Further research is needed to determine its full therapeutic potential and to evaluate its safety and efficacy in clinical trials.

Potential Implications in Various Fields of Research and Industry

[(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate has potential implications in various fields of research and industry. Its use as a lead compound for the development of new anticancer and antimicrobial agents could benefit the pharmaceutical industry. Its potential as a tubulin polymerization inhibitor could lead to the development of new drugs that target cell proliferation and division. [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate’s antimicrobial properties could also have implications for the development of new antimicrobial agents.

Limitations and Future Directions

Despite its promising potential, there are limitations to [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate’s current research. One limitation is the limited research on its safety and toxicity. Future research should focus on evaluating the long-term effects of [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate exposure and its safety in clinical trials. Additionally, there is a need for better analytical methods to ensure the accuracy of [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate’s purity and concentration. Finally, further studies are needed to determine the potential applications of [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate in other fields of research and industry.

Future Directions

There are a number of potential future directions for research on [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate. Some of these include:

- Investigating the effects of [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate on other types of cancer cells.

- Determining the potential applications of [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate in other fields of research such as neuroscience and immunology.

- Exploring alternative synthetic routes for [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate that reduce its environmental impact.

- Developing better analytical methods to quantify [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate in complex biological matrices.

- Investigating the potential use of [(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate in combination with other drugs for enhanced anticancer and antimicrobial activity.

Conclusion

[(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate is a promising compound with potential applications in various fields of research and industry, including anticancer and antimicrobial research. Its tubulin polymerization inhibition properties show potential for the development of new drugs that target cell proliferation and division. However, more research is needed to fully understand its therapeutic potential, safety, and efficacy in clinical trials. Future research should also focus on exploring alternative synthetic routes and developing better analytical methods to ensure its accuracy and reduce its environmental impact.

CAS Number14125-75-8
Product Name[(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate
     Synonyms

    tetra-O-benzoyl-D-arabino-hex-1-enitol;

    2,3,4,6-tetra-O-benzoyl-1,5-anhydro-D-arabino-hex-1-enitol;

    tetra-O-benzoyl-1,5-anhydro-D-arabino-hex-1-enitol;

    2,3,4,6-tetra-O-benzoyl-D-hydroxyglucal;

    1-Deoxy-D-gluco-hex-1-enopyranose tetrabenzoate;

    2,3,4,6-tetra-O-benzoyl-2-hydroxy-D-glucal;

    Tetra-O-benzoyl-1,5-anhydro-D-arabino-hex-1-enit;

    1,5-anhydro-2,3,4,6-tetra-O-benzoyl-D-arabino-hex-1-enitol;

IUPAC Name[(2R,3R,4S)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate
Molecular FormulaC34H26O9
Molecular Weight578.56 g/mol
InChIInChI=1S/C34H26O9/c35-31(23-13-5-1-6-14-23)40-21-27-29(42-33(37)25-17-9-3-10-18-25)30(43-34(38)26-19-11-4-12-20-26)28(22-39-27)41-32(36)24-15-7-2-8-16-24/h1-20,22,27,29-30H,21H2/t27-,29-,30-/m1/s1
InChI KeyHHNQKUIYTNDYHW-MJLPRTPSSA-N
SMILESC1=CC=C(C=C1)C(=O)OCC2C(C(C(=CO2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5
Canonical SMILESC1=CC=C(C=C1)C(=O)OCC2C(C(C(=CO2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5
Isomeric SMILESC1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H]([C@@H](C(=CO2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5

CAS No: 14125-75-8 Synonyms: 2,3,4,6-Tetra-O-benzoyl-2-hydroxy-D-glucal  ,1-Deoxy-D-gluco-hex-1-enopyranose tetrabenzoate MDL No: MFCD00010693 

Chemical Formula: C34H26O9 Molecular Weight: 578.56


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