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3934-29-0 , a-D-Glucopyranosyl fluoride tetraacetate , CAS: 3934-29-0

3934-29-0 , a-D-Glucopyranosyl fluoride tetraacetate ,
CAS:3934-29-0
C14H19FO9 / 350.29
MFCD00792705

a-D-Glucopyranosyl fluoride tetraacetate

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 CH2Cland

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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