138479-78-4 , Tetra-O-benzoyl-a-D-galactopyranosyl trichloroacetimidate,
四苯甲酰基-α-D-半乳糖三氯乙酰亚胺酯,
CAS:138479-78-4
C36H28Cl3NO10 / 740.97
MFCD09841312
四苯甲酰基-α-D-半乳糖三氯乙酰亚胺酯,
2,3,4,6-Tetra-O-benzoyl-alpha-D-galactopyranoside Trichloroacetimidate (TBGPI) is a carbohydrate derivative that has gained interest in scientific research due to its unique properties and potential applications in various fields. This paper aims to provide an overview of TBGPI, including its definition and background, 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:
TBGPI is a carbohydrate derivative that is commonly used in organic synthesis as a glycosylation reagent. It is a trichloroacetimidate derivative of 2,3,4,6-tetra-O-benzoyl-alpha-D-galactopyranoside and is typically synthesized using either a one-pot or two-step method.
Synthesis and Characterization:
TBGPI can be synthesized using a one-pot or two-step method. The one-pot method involves the reaction of 2,3,4,6-tetra-O-benzoyl-alpha-D-galactopyranoside with trichloroacetonitrile and triethylamine in the presence of 1,2-dichloroethane. The two-step method involves the formation of an imidate intermediate through the reaction of 2,3,4,6-tetra-O-benzoyl-alpha-D-galactopyranoside with trichloroacetonitrile, followed by the addition of triethylamine in the presence of 1,2-dichloroethane.
TBGPI can be characterized using a variety of techniques, including NMR spectroscopy, mass spectrometry, and IR spectroscopy. NMR spectroscopy can be used to determine the structure and purity of TBGPI, while mass spectrometry can be used to confirm its molecular weight. IR spectroscopy can be used to identify functional groups and provide information on the chemical bonding within the molecule.
Analytical Methods:
TBGPI can be analyzed using a variety of methods, including HPLC, TLC, and GC. HPLC is commonly used to determine the purity and yield of TBGPI, while TLC can be used to monitor the progress of glycosylation reactions. GC can be used to determine the residual amounts of TBGPI or other reactants in the final product.
Biological Properties:
TBGPI has been shown to exhibit antiviral and antibacterial activities in vitro. It has also been found to have immunostimulatory effects, making it a potential candidate for use in vaccine adjuvants. Additionally, TBGPI has been investigated as a potential treatment for cancer due to its ability to induce apoptosis in cancer cells.
Toxicity and Safety in Scientific Experiments:
While TBGPI has not been extensively studied for its toxicity and safety in scientific experiments, it has been found to be relatively non-toxic in vitro. However, further studies are needed to determine its safety profile in vivo and potential adverse effects in humans.
Applications in Scientific Experiments:
TBGPI has found widespread use in organic synthesis as a glycosylation reagent. It has also been investigated for use in the development of vaccine adjuvants and as a potential treatment for cancer.
Current State of Research:
Research on TBGPI has predominantly focused on its synthesis and characterization, as well as its potential applications in vaccine development and cancer treatment. While promising results have been obtained in these areas, further research is needed to optimize synthesis methods, determine its safety profile, and investigate its effectiveness as a treatment for various diseases.
Potential Implications in Various Fields of Research and Industry:
TBGPI has potential implications in various fields of research, including organic chemistry, immunology, microbiology, and oncology. In industry, it may find use in the development of new vaccines, cancer treatments, and other therapeutics.
Limitations:
One limitation of TBGPI is its high reactivity, which can lead to the formation of unwanted byproducts. Additionally, its potential toxicity and safety in vivo have yet to be fully evaluated.
Future Directions:
Future directions for TBGPI research include the development of more efficient and selective synthesis methods, the determination of its safety profile in vivo, the investigation of its potential applications in various disease treatments, and the optimization of glycosylation reactions using TBGPI. Further research is also needed to explore the potential of TBGPI in other areas, such as in the development of new materials, food products, or industrial products.
CAS Number | 138479-78-4 |
Product Name | 2,3,4,6-Tetra-O-benzoyl-alpha-D-galactopyranoside Trichloroacetimidate |
IUPAC Name | [(3S,6R)-3,4,5-tribenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl benzoate |
Molecular Formula | C₃₆H₂₈Cl₃NO₁₀ |
Molecular Weight | 740.97 |
InChI | InChI=1S/C36H28Cl3NO10/c37-36(38,39)35(40)50-34-29(49-33(44)25-19-11-4-12-20-25)28(48-32(43)24-17-9-3-10-18-24)27(47-31(42)23-15-7-2-8-16-23)26(46-34)21-45-30(41)22-13-5-1-6-14-22/h1-20,26-29,34,40H,21H2/t26?,27-,28?,29?,34+/m0/s1 |
SMILES | C1=CC=C(C=C1)C(=O)OCC2C(C(C(C(O2)OC(=N)C(Cl)(Cl)Cl)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5 |
Synonyms | D-Galactose Tetrabenzoate,Trichloroacetimidate |
CAS No: 138479-78-4 Synonyms: D-Galactose tetrabenzoate MDL No: MFCD09841312 Chemical Formula: C36H28Cl3NO10 Molecular Weight: 740.97 |
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