1941-52-2 ,D-Glucose diethyl dithioacetal,
CAS:1941-52-2
C10H22O5S2 / 286.41
MFCD00004706
D-葡萄糖缩二乙硫醇,
D-Glucose diethyl mercaptal is a homogeneous catalyst that can be used to acetylate galactitol to produce D-arabinose. It acts as an efficient and selective catalyst for the reaction of nitrous acid with hydrochloric acid, which produces acetyl chloride. Acetyl chloride is a reactive compound that can be used in the synthesis of many other compounds. D-Glucose diethyl mercaptal has been used in chromatographic methods to separate d-arabinose from L-arabinose. The ring-opening polymerization of D-glucopyranose by mercaptals leads to the formation of polyols, which are useful materials for the production of plastics and rubber products. Chloride ions are required for this reaction, while hydrogen chloride is produced as a byproduct.
D-Glucose diethyl dithioacetal (DTD) is a thioacetal derivative of glucose, also known as 1,2-anhydro-3,4-di-O-ethyl-D-glucopyranose-5-thioacetate. DTD is a small molecule that can play a significant role in various fields of research and industry, including organic synthesis, drug design, and material science. DTD is widely used as a building block in the construction of complicated carbohydrate derivatives.
Physical and Chemical Properties
DTD is a colorless liquid that possesses a sweet odor with a molecular formula of C10H22O5S2 and a molecular weight of 286.41 g/mol. It is soluble in many polar organic solvents, including alcohols, ethers, and chloroform, and insoluble in nonpolar organic solvents. DTD is a relatively stable compound except near strong acids or bases, where it is hydrolyzed.
Synthesis and Characterization
DTD can be synthesized by the reaction of glucose with diethyl carbon disulfide in the presence of a strong base, such as potassium hydroxide. The reaction mechanism involves the removal of a proton from the carbon atom adjacent to the anomeric carbon, followed by nucleophilic attack by the dithioacetal moiety of the diethyl carbon disulfide. The product can be isolated and then purified by various methods, including column chromatography and recrystallization. DTD can be characterized by various spectroscopic techniques, including NMR, infrared spectroscopy, and mass spectrometry.
Analytical Methods
Several analytical methods are used for the detection and quantification of DTD, including high-performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS). HPLC with a refractive index detector can detect DTD at picogram levels, making it a useful tool for monitoring DTD concentration in biological fluids. GC-MS is a highly sensitive method that can analyze DTD in complex sample matrices with high accuracy and precision.
Biological Properties
DTD has several biological properties that make it a useful tool for biological research. It is a non-toxic compound that can be used as a carbohydrate source by various microorganisms and as a substrate for enzymatic reactions. DTD has also been shown to possess antifungal activity against various fungal species, including Candida albicans, Aspergillus flavus, and Fusarium oxysporum.
Toxicity and Safety in Scientific Experiments
DTD is generally considered to be a safe compound, with low toxicity and minimal environmental impact. However, as with any chemical reagent, safe handling and disposal procedures should be followed. In scientific experiments, appropriate safety measures should be taken to minimize the risk of exposure to DTD and other hazardous chemicals.
Applications in Scientific Experiments
DTD has several applications in scientific experiments, including organic synthesis, material science, and drug design. DTD can be used as a starting material for the synthesis of various carbohydrate derivatives, including glycosides, oligosaccharides, and polysaccharides. DTD can also be incorporated into polymer networks to create novel hydrogels with potential applications in drug delivery and tissue engineering. In drug design, DTD can be used as a building block for the development of carbohydrate-based drugs.
Current State of Research
Research on DTD has been ongoing for several decades, with significant progress made in the synthesis, characterization, and application of DTD and its derivatives. Recent research has focused on the development of new synthetic methods and the exploration of DTD's potential applications in drug design, organic synthesis, and material science.
Potential Implications in Various Fields of Research and Industry
DTD has the potential to have significant implications in various fields of research and industry. In drug design, carbohydrate-based drugs are currently under investigation for the treatment of various diseases, including cancer, viral infections, and inflammation. In material science, DTD and its derivatives can be used to create novel hydrogels with potential applications in tissue engineering and drug delivery. DTD can also be a useful building block in the development of new synthetic routes for the synthesis of complex carbohydrates.
Limitations and Future Directions
Despite the significant progress made in the study of DTD, limitations still exist. DTD is relatively expensive, and the synthesis requires the use of hazardous chemicals. Future research could focus on developing cost-effective and sustainable synthetic methods for the large-scale production of DTD. Additionally, further investigations are needed to explore the full potential of DTD and its derivatives in various fields of research and industry.
Future Directions:
- Investigation of DTD's potential as a metal scavenger
- Development of sustainable synthetic routes for DTD
- Exploration of the use of DTD in biocatalysis and enzyme immobilization
- Investigation of the potential of DTD as a precursor for the synthesis of biodegradable polymers
- Exploration of the use of DTD in drug delivery via nanocarrier systems
- Investigation of DTD and its derivatives for the treatment of various diseases, including diabetes and Alzheimer's disease
- Exploration of the use of DTD in the synthesis of bioactive natural products
- Investigation of the potential of DTD as a template for the synthesis of bioactive peptides
- Exploration of the use of DTD in the development of biosensors for the detection of various analytes
- Investigation of the use of DTD in water purification and desalination processes.
CAS Number | 1941-52-2 |
Product Name | D-Glucose diethyl dithioacetal |
IUPAC Name | (2R,3R,4S,5R)-6,6-bis(ethylsulfanyl)hexane-1,2,3,4,5-pentol |
Molecular Formula | C10H22O5S2 |
Molecular Weight | 286.41 g/mol |
InChI | InChI=1S/C10H22O5S2/c1-3-16-10(17-4-2)9(15)8(14)7(13)6(12)5-11/h6-15H,3-5H2,1-2H3/t6-,7-,8+,9-/m1/s1 |
InChI Key | BTOYCPDACQXQRS-LURQLKTLSA-N |
SMILES | CCSC(C(C(C(C(CO)O)O)O)O)SCC |
Canonical SMILES | CCSC(C(C(C(C(CO)O)O)O)O)SCC |
Isomeric SMILES | CCSC([C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)SCC |
CAS No: 1941-52-2 Synonyms: D-Glucose diethyldithioacetal MDL No: MFCD00004706 Chemical Formula: C10H22O5S2 Molecular Weight: 286.41 |
References: 1. Lipták M, Dinya Z, Sztaricskai FJ, Litkei G, Jekö J, Org. Mass Spectrom. Vol 27, 11, 1271-12752. Wolfrom ML, Weisblat DI, Hanze AR, J. Am. Chem. Soc. 1944, Dec, p2065 |
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