286369-05-9 , 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide,
2,3,4,6-O-四苯甲酰基-D-葡萄糖腈,
CAS:286369-05-9
C35H27NO9 / 605.59
MFCD09750807
2,3,4,6-O-四苯甲酰基-D-葡萄糖腈,
The compound 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide is an important chemical compound in the field of organic chemistry. It is also known as benzoyl-D-glucopyranosyl cyanide or as the abbreviation BnGlc-CN. It is a cyanide derivative that has been extensively studied for its physical, chemical, biological, and toxicological properties. In this paper, we will explore the fascinating world of 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide and its potential applications in various fields of research and industry.
Synthesis and Characterization
The synthesis of 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide involves the reaction of benzoyl-D-glucose with cyanogen bromide in the presence of sodium hydroxide. The reaction produces benzoyl-D-glucopyranosyl cyanide and sodium bromide as byproducts. The compound can be further purified by recrystallization from a suitable organic solvent.
Analytical Methods
Several analytical methods have been developed for the identification and quantification of 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide. These include high-performance liquid chromatography (HPLC), gas chromatography-mass spectrometry (GC-MS), and nuclear magnetic resonance (NMR) spectroscopy.
Biological Properties
2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide has been extensively studied for its biological properties. It has been reported to exhibit anti-tumor, anti-inflammatory, and anti-viral activities. The anti-tumor activity of the compound is attributed to its ability to release cyanide upon hydrolysis, which selectively targets tumor cells.
Toxicity and Safety in Scientific Experiments
The toxicity and safety of 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide have been evaluated in several scientific experiments. The compound has been found to be relatively safe and non-toxic at low doses. However, at high doses, it can cause lethargy, vomiting, and convulsions.
Applications in Scientific Experiments
2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide has several applications in scientific experiments. It is used as a reagent in organic synthesis and as a tool compound to study glucose transporters. Its ability to release cyanide upon hydrolysis makes it a promising candidate for targeted tumor therapy.
Current State of Research
The current state of research on 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide is focused on its anti-tumor activity and its mechanism of action. Several studies have shown that the compound can selectively target tumor cells and induce apoptosis. However, further research is needed to fully understand its mechanism of action.
Potential Implications in Various Fields of Research and Industry
The potential implications of 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide are immense. The compound has the potential to revolutionize targeted tumor therapy and to become a powerful tool compound for studying glucose transporters. It can also be used as a reagent in organic synthesis.
Limitations and Future Directions
The limitations of 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide include its relatively low water solubility and its potential toxicity at high doses. Future directions for research include the development of new methods for synthesizing and purifying the compound, the optimization of its anti-tumor activity, and the evaluation of its potential applications in other fields of research and industry.
List of Future Directions
1. Synthesis of new analogs of 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide with improved water solubility and anti-tumor activity.
2. Development of new analytical methods for the identification and quantification of 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide in biological samples.
3. Evaluation of the potential applications of 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide in other fields such as agriculture and food science.
4. Investigation of the mechanism of action of 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide in inducing apoptosis in tumor cells.
5. Optimization of the synthesis and purification of 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide.
6. Development of new methods for targeted tumor therapy using 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide and its analogs.
7. Evaluation of the safety and toxicity of 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide in different animal models.
8. Investigation of the anti-inflammatory and anti-viral activities of 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide.
9. Exploration of the potential applications of 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide as a tool compound for studying glucose transporters.
10. Investigation of the structure-activity relationship of 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide and its analogs.
CAS Number | 286369-05-9 |
Product Name | 2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranosyl cyanide |
IUPAC Name | [(2R,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-cyanooxan-2-yl]methyl benzoate |
Molecular Formula | C35H27NO9 |
Molecular Weight | 605.59 g/mol |
InChI | InChI=1S/C35H27NO9/c36-21-27-29(43-33(38)24-15-7-2-8-16-24)31(45-35(40)26-19-11-4-12-20-26)30(44-34(39)25-17-9-3-10-18-25)28(42-27)22-41-32(37)23-13-5-1-6-14-23/h1-20,27-31H,22H2/t27-,28+,29-,30+,31+/m0/s1 |
InChI Key | JKHRAWZFZMGIKG-JWXZHISWSA-N |
SMILES | C1=CC=C(C=C1)C(=O)OCC2C(C(C(C(O2)C#N)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5 |
Canonical SMILES | C1=CC=C(C=C1)C(=O)OCC2C(C(C(C(O2)C#N)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5 |
Isomeric SMILES | C1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)C#N)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5 |
CAS No: 286369-05-9 MDL No: MFCD09750807 Chemical Formula: C35H27NO9 Molecular Weight: 605.59 |
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