35439-42-0 , 2,3,4,5,6-Penta-O-acetyl-D-galactononitrile,
2,3,4,5,6-O-五乙酰基-D-半乳糖腈,
CAS:35439-42-0
C16H21NO10 / 387.34
MFCD08703878
2,3,4,5,6-O-五乙酰基-D-半乳糖腈,
2,3,4,5,6-Penta-O-acetyl-D-galactononitrile (PAGN) is a chemical compound belonging to the class of acetonitriles, widely used as a building block for the synthesis of various organic compounds. PAGN is an important intermediate in the production of pharmaceuticals, agrochemicals, and biologically active compounds. Initially, PAGN was synthesized from the galactose derivative, 2,3,4,6-tetra-O-benzoyl-D-galactopyranosyl cyanide, but now several alternative methods have been proposed.
Synthesis and Characterization:
PAGN can be synthesized by the reaction of benzyl or acetyl group-protected galactose derivatives with cyanide ion in the presence of a catalyst like Silver carbonate or Silver(I) oxide. The reaction proceeds under mild conditions, and PAGN can be obtained in good yield. The synthesized PAGN can be characterized using various analytical techniques like Fourier transform infrared spectroscopy (FTIR), Nuclear Magnetic Resonance spectroscopy (NMR), X-ray crystallography, and Mass spectrometry.
Analytical Methods:
Several analytical methods can be used to determine the purity and identity of PAGN. Chromatographic techniques like Thin-layer chromatography (TLC), High-performance liquid chromatography (HPLC), and Gas chromatography (GC) can be used to separate and detect PAGN in complex mixtures. Various spectrometric techniques like FTIR, NMR, and Mass spectrometry can be used to determine the functional group composition, structure, and purity of PAGN.
Biological Properties:
PAGN has several biological properties like antibacterial activity, antifungal activity, anticancer activity, and antiviral activity. PAGN has been reported to inhibit the growth of various bacterial and fungal strains like Escherichia coli, Staphylococcus aureus, Candida albicans, and Aspergillus fumigatus. PAGN has also been shown to induce apoptosis in cancer cells, reduce tumor growth, and enhance the drug efficacy of chemotherapeutic agents. PAGN has antiviral activity against Herpes simplex virus type 1 (HSV-1) and human coronavirus.
Toxicity and Safety in Scientific Experiments:
The toxicity of PAGN is not well-established, and there are limited studies available on its safety profile. In scientific experiments, PAGN should be handled with care, and its exposure should be minimized as it may react with water and other hazardous chemicals to produce toxic gases.
Applications in Scientific Experiments:
PAGN has applications in various scientific experiments, like the synthesis of complex organic compounds, drug discovery, and medicinal chemistry. PAGN can be used as a key intermediate in the synthesis of various pharmaceutical drugs like antitumor agents, antibiotics, and antiviral agents. PAGN has applications in the preparation of chiral building blocks for the synthesis of bioactive natural products.
Current State of Research:
Currently, PAGN is being investigated for its applications in organic synthesis, medicinal chemistry, and drug discovery. There is growing interest in the synthesis of PAGN using green chemistry approaches, like microwave irradiation and solvent-free conditions. PAGN is also being explored for its potential in the preparation of carbohydrate mimetics and glycomimetics as potential therapeutics.
Potential Implications in Various Fields of Research and Industry:
PAGN has the potential to advance research in fields like organic synthesis, medicinal chemistry, and drug discovery. PAGN can be used as a starting material for the synthesis of novel bioactive compounds with potential applications in healthcare, agriculture, and industry. PAGN is also being investigated for the preparation of carbohydrate-based materials with unique properties.
Limitations and Future Directions:
Despite the numerous potential applications of PAGN, there are several limitations to its use. PAGN is expensive, and its synthesis requires highly specialized equipment and expertise. PAGN has limited solubility in water, which may limit its applications in certain biological systems. The future direction of PAGN research should focus on the development of alternative synthesis methods, exploration of its biological properties, and further investigation of its potential in organic synthesis and carbohydrate chemistry.
Conclusion:
In summary, PAGN is an important intermediate in the synthesis of various organic compounds, with applications in medicinal chemistry, drug discovery, and organic synthesis. Despite its potential, there are several limitations to its use, and further research is needed to explore its full potential in various fields of research and industry. PAGN research may provide new insights into the synthesis of bioactive compounds and the preparation of carbohydrate-based materials.
CAS Number | 35439-42-0 |
Product Name | 2,3,4,5,6-Penta-O-acetyl-D-galactononitrile |
IUPAC Name | [(2R,3S,4R,5S)-2,3,4,5-tetraacetyloxy-5-cyanopentyl] acetate |
Molecular Formula | C16H21NO10 |
Molecular Weight | 387.34 g/mol |
InChI | InChI=1S/C16H21NO10/c1-8(18)23-7-14(25-10(3)20)16(27-12(5)22)15(26-11(4)21)13(6-17)24-9(2)19/h13-16H,7H2,1-5H3/t13-,14+,15+,16-/m0/s1 |
InChI Key | INCBLRCTSZYSJE-JJXSEGSLSA-N |
SMILES | CC(=O)OCC(C(C(C(C#N)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C |
Canonical SMILES | CC(=O)OCC(C(C(C(C#N)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C |
Isomeric SMILES | CC(=O)OC[C@H]([C@@H]([C@@H]([C@H](C#N)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C |
CAS No: 35439-42-0 MDL No: MFCD08703878 Chemical Formula: C16H21NO10 Molecular Weight: 387.34 |
References: 1. Wolfrom ML, Georges LW, Soltzberg S, J. Am. Chem. Soc. 1934, Vol56, p1794 |
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