146788-09-2 , Ethyl 2,3,6,2',3',4',6'-hepta-O-acetyl-D-thiolactopyranoside
Ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-b-D-galactopyranosyl)-D-thioglucopyranoside
C28H40O17S / 680.672
MFCD09750886
Ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-b-D-galactopyranosyl)-D-thioglucopyranoside
Ethyl 2,3,6,2',3',4',6'-Hepta-O-acetyl-α,β-D-thiolactopyranoside, also known as EHP, is a derivative of D-thiolactopyranose, which is an important building block in carbohydrates. Its unique structure and properties have attracted attention from researchers in various fields, including chemistry, biology, and medicine. This paper will provide a comprehensive overview of EHP, 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.
Physical and Chemical Properties
EHP has some unique physical and chemical properties that make it an attractive building block for various applications. It has a high melting point of around 195-196°C, which makes it a stable compound under most conditions. EHP is also soluble in various organic solvents and slightly soluble in water, indicating its potential use in different types of reactions.
The chemical properties of EHP are also important for understanding its potential applications. EHP contains thiol groups, which are essential for its use as a protecting group in carbohydrate synthesis. These thiol groups can be selectively removed under suitable conditions, leading to the deprotection of the corresponding protected carbohydrate.
Synthesis and Characterization
EHP can be synthesized using various methods, depending on the desired application. One common method is the reaction of D-thiolactopyranose with ethyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide in the presence of a suitable base, such as sodium hydride, in a solvent like dimethylformamide. This reaction yields EHP as a crystalline solid.
Characterization of EHP typically involves the use of various analytical techniques, such as nuclear magnetic resonance spectroscopy, mass spectrometry, and infrared spectroscopy. These techniques can be used to identify the structure of EHP and monitor the progress of the synthesis.
Analytical Methods
Various analytical methods can be used to quantify the amount of EHP in a given sample and to assess its purity. These methods include high-performance liquid chromatography, mass spectrometry, and nuclear magnetic resonance spectroscopy. These techniques can also be used to monitor reactions involving EHP and to study its reactivity in different solvents and under different conditions.
Biological Properties
Various studies have been conducted to assess the biological properties of EHP and its potential applications. For example, EHP has been reported to exhibit antibacterial properties against certain strains of bacteria, such as Staphylococcus aureus. EHP has also shown potential as an anticancer agent, as it can inhibit the growth of cancer cells in vitro.
Toxicity and Safety in Scientific Experiments
Toxicity and safety of EHP in scientific experiments can be assessed by conducting appropriate experiments, such as toxicity assays in vitro, in vivo, and in animal models. These experiments can help identify any potential adverse effects of EHP and determine the safety of its use in different applications.
Applications in Scientific Experiments
EHP has various applications in scientific experiments, particularly in the fields of chemistry, biology, and medicine. One of the most common uses of EHP is as a protecting group in carbohydrate synthesis, as mentioned earlier. EHP can also be used as a reactant or precursor in various types of reactions, such as Suzuki-Miyaura coupling and Heck coupling.
Current State of Research
There is ongoing research on EHP and its potential applications in various fields. For example, researchers are exploring the potential of EHP as an antibacterial agent and as an anticancer drug. Other studies are focused on developing new synthetic routes for EHP and its derivatives to improve their properties and increase their yields.
Potential Implications in Various Fields of Research and Industry
EHP has potential implications in various fields of research and industry due to its unique properties. For example, it can be used as a building block in the synthesis of various carbohydrates, which have potential applications in drug discovery and materials science. EHP and its derivatives can also be used in the production of chemical intermediates, such as chiral compounds, that have potential uses in various industries.
Limitations and Future Directions
Despite its potential applications, EHP has some limitations that need to be addressed in future research. For example, EHP can be expensive to synthesize, and the yields of certain reactions involving EHP can be low. Future research could focus on developing more efficient synthetic routes and improving the yields of these reactions. Other areas of research could include the optimization of conditions for the deprotection of EHP and the development of new applications for EHP and its derivatives.
In conclusion, EHP is a derivative of D-thiolactopyranose that has attracted attention from researchers in various fields due to its unique properties and potential applications. This paper has provided a comprehensive overview of EHP, 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.
Chemical Name | ethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside |
Synonyms | Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-ethylsulfanyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester; |
CAS No. | 146788-09-2 |
Molecular Formula | C28H40O17S |
Molecular Weight | 680.67200 |
PSA | 237.09000 |
LogP | 0.35920 |
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