86520-63-0 ,Tetra-O-acetyl-a-D-galactopyranosyl trichloroacetimidate ,
四乙酰-alpha-D-半乳糖三氯乙酰亚胺酯,
CAS: 86520-63-0
C16H20Cl3NO10 / 492.69
MFCD07369652
四乙酰-alpha-D-半乳糖三氯乙酰亚胺酯,
2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl trichloroacetimidate is a disaccharide that is an activated glycoprotein. It is used as a hapten for the production of monoclonal antibodies and as an immunogen in stepwise immunization with bovine serum albumin. This compound has been shown to be specific for the EGF receptor on neoglycoproteins and can be used to detect this receptor. The glycosidic residue of 2,3,4,6-tetra-O-acetyl-a-D-galactopyranosyl trichloroacetimidate allows it to bind to proteins such as albumin and act as a carrier for other molecules.
2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl trichloroacetimidate is an organotin compound used in carbohydrate chemistry as a glycosylating agent. It is considered a highly effective reagent in the synthesis of oligosaccharides and glycosides. Oligosaccharides and glycosides are important biomolecules involved in various physiological and pathological processes.
Synthesis and Characterization
The synthesis of 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl trichloroacetimidate can be achieved through a reaction between trichloroacetonitrile and the corresponding carbohydrate derivative. The reaction is carried out under mild conditions and yields a highly pure product. The compound is characterized by various techniques such as nuclear magnetic resonance spectroscopy, mass spectrometry, and infrared spectroscopy.
Analytical Methods
2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl trichloroacetimidate can be analyzed using various techniques such as high-performance liquid chromatography, gas chromatography, and thin-layer chromatography. These techniques are used to determine the purity and identity of the compound.
Biological Properties
2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl trichloroacetimidate has been shown to exhibit antibacterial and antifungal properties in vitro. It has also been found to inhibit the growth of cancer cells in vitro. However, its biological properties are still under investigation, and further studies are needed to fully understand its potential in the field of medicine.
Toxicity and Safety in Scientific Experiments
Studies have shown that 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl trichloroacetimidate exhibits low toxicity in vivo. However, caution should be taken when handling the compound, as it is classified as a hazardous material.
Applications in Scientific Experiments
2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl trichloroacetimidate is widely used in the synthesis of oligosaccharides and glycosides. Its effectiveness and low toxicity make it a popular choice for carbohydrate synthesis. It is also used as a reagent in the synthesis of glycomimetics and other glycoconjugates.
Current State of Research
Research on 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl trichloroacetimidate is ongoing. Studies are being conducted to investigate its potential in the fields of medicine, biotechnology, and materials science. Research is also being carried out to develop new synthetic methods using this reagent.
Potential Implications in Various Fields of Research and Industry
2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl trichloroacetimidate has potential applications in various fields of research and industry. In the field of medicine, it could be used in the synthesis of oligosaccharides involved in drug discovery and development. In biotechnology, it could be used in the development of new glycoconjugates with improved properties. In materials science, it could be used in the synthesis of new functional materials with specific carbohydrate structures.
Limitations and Future Directions
Despite its effectiveness in carbohydrate synthesis, 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl trichloroacetimidate has some limitations. Its high cost and sensitivity to air and moisture make it difficult to handle. Future research should focus on improving synthetic methods to reduce the cost of production and developing new derivatives with improved stability. Other future directions include the investigation of its potential in the synthesis of complex oligosaccharides and the development of new analytical methods for its detection and analysis.
In conclusion, 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl trichloroacetimidate is an important reagent in carbohydrate chemistry with potential applications in various fields of research and industry. Its effectiveness, low toxicity, and biological properties make it a promising tool in the synthesis of oligosaccharides and glycoconjugates. Further research is needed to fully understand its potential and overcome its limitations.
CAS Number | 86520-63-0 |
Product Name | 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl trichloroacetimidate |
IUPAC Name | [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate |
Molecular Formula | C16H20Cl3NO10 |
Molecular Weight | 492.69 g/mol |
InChI | InChI=1S/C16H20Cl3NO10/c1-6(21)25-5-10-11(26-7(2)22)12(27-8(3)23)13(28-9(4)24)14(29-10)30-15(20)16(17,18)19/h10-14,20H,5H2,1-4H3/t10-,11+,12+,13-,14-/m1/s1 |
InChI Key | IBUZGVQIKARDAF-MBJXGIAVSA-N |
SMILES | CC(=O)OCC1C(C(C(C(O1)OC(=N)C(Cl)(Cl)Cl)OC(=O)C)OC(=O)C)OC(=O)C |
Synonyms | α-D-Galactopyranose, 2,3,4,6-Tetraacetate 1-(2,2,2-Trichloroethanimidate) |
Canonical SMILES | CC(=O)OCC1C(C(C(C(O1)OC(=N)C(Cl)(Cl)Cl)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)OC(=N)C(Cl)(Cl)Cl)OC(=O)C)OC(=O)C)OC(=O)C |
CAS No: 86520-63-0 MDL No: MFCD07369652 Chemical Formula: C16H20Cl3NO10 Molecular Weight: 492.69 |
References: 1. Sasaki K, Nishida Y, Tsurumi T, Uzawa H, Kondo H, et al., Angew Chem. Int. Ed. 2002, Vol41, Pt23, p4463-4467 |
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