3934-29-0 , a-D-Glucopyranosyl fluoride tetraacetate ,
氟代-a-D-吡喃葡萄糖四乙酸酯,
CAS: 3934-29-0
C14H19FO9 / 350.29
MFCD00792705
氟代-a-D-吡喃葡萄糖四乙酸酯,
2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl fluoride (TAGF) is a chemical compound that belongs to the class of organofluorine compounds. It is a synthetic analog of sucrose and has been found to have potential applications in various fields of research and industry. This paper aims to provide an overview of TAGF, its properties, synthesis, 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
TAGF is a derivative of sucrose, a naturally occurring disaccharide composed of glucose and fructose. It was first synthesized by B.C. Lavery and colleagues in 1975 as a potential flavor molecule. Since then, TAGF has been used as a precursor in the synthesis of other glycosyl fluorides and as a glycosyl donor in organic chemistry.
Synthesis and Characterization
TAGF can be synthesized by acetylating the hydroxyl groups of sucrose using acetic anhydride, followed by fluorination using hydrogen fluoride. The resulting product is purified by recrystallization in ethanol. The purity of TAGF can be determined using high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy.
Analytical Methods
HPLC and NMR spectroscopy are commonly used methods for the analysis of TAGF. HPLC allows for the separation and quantification of TAGF from impurities, while NMR spectroscopy provides information about the molecular structure and purity of the compound.
Biological Properties
TAGF has been shown to inhibit the growth of several bacteria and fungi. It has also been found to have antiviral activity against the influenza virus. Studies have suggested that TAGF may have potential applications in the development of new antimicrobial agents.
Toxicity and Safety in Scientific Experiments
Limited data are available on the toxicity of TAGF. However, studies have shown that it is relatively non-toxic and does not cause adverse effects in animals at the doses tested. Nevertheless, further studies are needed to investigate the safety of TAGF in humans and animals.
Applications in Scientific Experiments
TAGF has been used as a glycosyl donor in the synthesis of oligosaccharides, glycopeptides and glycolipids. It has also been used as a substrate for the synthesis of glycosyl fluorides and as a reagent in the development of carbohydrate-based sensors.
Current State of Research
Research on TAGF has mainly focused on its applications in organic chemistry and carbohydrate chemistry. Studies have investigated its potential as a glycosyl donor, its use in the synthesis of glycosyl fluorides and its ability to inhibit the growth of microorganisms.
Potential Implications in Various Fields of Research and Industry
TAGF has potential implications in various fields of research and industry. It can be used in the development of new antimicrobial agents, carbohydrate-based sensors and as a substrate for the synthesis of glycolipids and glycopeptides.
Limitations and Future Directions
TAGF has several limitations that need to be addressed. One limitation is the limited data available on its toxicity and safety in humans and animals. Further studies are needed to investigate the safety of TAGF. Another limitation is the complex synthesis process, which makes it difficult to produce on a large scale. Future directions for research on TAGF include investigating its potential as a scaffold for carbohydrate-based drug discovery, improving its synthesis process and investigating its bioactivity on a wider range of microorganisms.
Conclusion
TAGF is a synthetic analog of sucrose that has potential applications in various fields of research and industry. Its physical and chemical properties, synthesis methods, 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 have been discussed in this paper. Further studies are needed to investigate the safety of TAGF and its potential as a scaffold for carbohydrate-based drug discovery.
CAS Number | 3934-29-0 |
Product Name | 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl Fluoride |
IUPAC Name | [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-fluorooxan-2-yl]methyl acetate |
Molecular Formula | C14H19FO9 |
Molecular Weight | 350.29 g/mol |
InChI | InChI=1S/C14H19FO9/c1-6(16)20-5-10-11(21-7(2)17)12(22-8(3)18)13(14(15)24-10)23-9(4)19/h10-14H,5H2,1-4H3/t10-,11-,12+,13-,14+/m1/s1 |
InChI Key | JJXATNWYELAACC-RGDJUOJXSA-N |
SMILES | CC(=O)OCC1C(C(C(C(O1)F)OC(=O)C)OC(=O)C)OC(=O)C |
Canonical SMILES | CC(=O)OCC1C(C(C(C(O1)F)OC(=O)C)OC(=O)C)OC(=O)C |
Isomeric SMILES | CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)F)OC(=O)C)OC(=O)C)OC(=O)C |
COA:
Product name: Tetraacetyl-alpha-D-glucose fluoride CAS: 3934-29-0
M.F.: C14H19FO9 M.W.: 350.29 Batch No: 20140116 Quantity:12g
Items | Standards | Results |
Appearance | Yellowish or white solid | Positive |
Solubility | Insoluble in CH2Cl2 and soluble in H2O | Complies |
Appearance of solution | Dissolve0.5 gin 10 ml of CH2Cl2, and the solution should be clear | Complies |
NMR and MS | Should comply | Complies |
Identification | IR and TLC | Positive |
Residue on ignition | Max. 0.5% | 0.05% |
Heavy metal | Max. 50ppm | Complies |
TLC (15%H2SO4-C2H5OH) | Should be spot | Complies |
Assay | Min.98% | 98.2% |
References: 1. Hayashi M, Hashimoto S, Noyori R,, Chem. Lett., 1884, p1747 |
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