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  • 4435-05-6 , 3,4,6-O-三乙酰基-b-D-吡喃甘露糖-1,2-原酸甲酯, CAS:4435-05-6
4435-05-6 , 3,4,6-O-三乙酰基-b-D-吡喃甘露糖-1,2-原酸甲酯, CAS:4435-05-6

4435-05-6 , 3,4,6-O-三乙酰基-b-D-吡喃甘露糖-1,2-原酸甲酯, CAS:4435-05-6

4435-05-6 ,3,4,6-Tri-O-acetyl-b-D-mannopyranose 1,2-(methyl orthoacetate),
3,4,6-O-三乙酰基-b-D-吡喃甘露糖-1,2-原酸甲酯,
CAS:4435-05-6
C15H22O10 / 362.33
MFCD00211213

3,4,6-Tri-O-acetyl-b-D-mannopyranose 1,2-(methyl orthoacetate)

3,4,6-O-三乙酰基-b-D-吡喃甘露糖-1,2-原酸甲酯,

3,4,6-Tri-O-acetyl-beta-D-mannopyranose 1,2-(methyl orthoacetate) is a synthetic compound with the chemical formula C15H24O10. It is commonly used as a building block for the synthesis of more complex molecules due to its reactivity and versatility. This chemical compound belongs to the family of beta-D-mannopyranoses, which are polysaccharides that occur naturally in several plants and tree barks.

Synthesis and Characterization

The synthesis of 3,4,6-Tri-O-acetyl-beta-D-mannopyranose 1,2-(methyl orthoacetate) involves the reaction of mannose with acetic anhydride and methyl orthoacetate in the presence of a catalyst such as p-toluenesulfonic acid (PTSA). The product is then purified by column chromatography or recrystallization. The compound's structure and purity can be determined using various techniques such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry.

Analytical Methods

The analytical methods used to detect and quantify 3,4,6-Tri-O-acetyl-beta-D-mannopyranose 1,2-(methyl orthoacetate) include high-performance liquid chromatography (HPLC) and gas chromatography (GC). HPLC is commonly used due to its high sensitivity and selectivity. GC can also be used to analyze the compound by converting it to its corresponding trimethylsilyl derivative.

Biological Properties

3,4,6-Tri-O-acetyl-beta-D-mannopyranose 1,2-(methyl orthoacetate) has been shown to exhibit several biological properties, including antitumor and immunostimulatory activities. Studies have also shown that the compound can stimulate macrophages and enhance the production of cytokines, which are essential components of the immune system. Additionally, this compound can also increase the survival rate of animals infected with viruses such as herpes simplex virus (HSV).

Toxicity and Safety in Scientific Experiments

Studies have shown that 3,4,6-Tri-O-acetyl-beta-D-mannopyranose 1,2-(methyl orthoacetate) is relatively safe and non-toxic. However, at higher doses, it may cause mild irritation and slight eye irritation. The compound should be handled with care, and appropriate protective equipment should be worn to minimize any potential hazards.

Applications in Scientific Experiments

3,4,6-Tri-O-acetyl-beta-D-mannopyranose 1,2-(methyl orthoacetate) has widespread applications in scientific research, including:

1. As a starting material for the synthesis of more complex molecules, such as glycoconjugates.

2. As a tool for the study of carbohydrate-protein interactions.

3. As an adjuvant in vaccines to enhance the immune response.

4. As a potential therapeutic agent for cancer and viral infections.

Current State of Research

Research on 3,4,6-Tri-O-acetyl-beta-D-mannopyranose 1,2-(methyl orthoacetate) is still ongoing, with scientists exploring its potential applications in various fields of research and industry.

Potential Implications in Various Fields of Research and Industry

There are several potential implications of 3,4,6-Tri-O-acetyl-beta-D-mannopyranose 1,2-(methyl orthoacetate) in various fields, including:

1. Medicine: Due to its immunostimulatory and antitumor properties, the compound may have potential applications in the development of new cancer therapies and vaccines.

2. Agriculture: The compound can be used as a plant growth regulator and may have applications in crop yield improvement.

3. Polymer chemistry: This compound can be used as a starting material to prepare novel biodegradable polymers.

Limitations and Future Directions

Although 3,4,6-Tri-O-acetyl-beta-D-mannopyranose 1,2-(methyl orthoacetate) has several potential applications, there are some limitations. For instance, the synthetic route to produce the compound is costly and time-consuming. Additionally, further studies are needed to investigate the structure-activity relationship of this compound and to optimize its biological properties for specific applications.

In the future, researchers may explore the following directions:

1. Developing more efficient and cost-effective synthetic routes to produce the compound.

2. Investigating the compound's potential applications in drug delivery systems.

3. Exploring the use of the compound as a bio-inspired material for several applications, including glucose sensing and bioimaging.

4. furthering the study of the compound's mechanism of action in various biological processes.

CAS Number4435-05-6
Product Name3,4,6-Tri-O-acetyl-beta-D-mannopyranose 1,2-(methyl orthoacetate)
IUPAC Name[(3aS,5R,6R,7S,7aS)-6,7-diacetyloxy-2-hydroxy-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate
Molecular FormulaC15H22O10
Molecular Weight362.33 g/mol
InChIInChI=1S/C14H20O10/c1-6(15)19-5-9-10(20-7(2)16)11(21-8(3)17)12-13(22-9)24-14(4,18)23-12/h9-13,18H,5H2,1-4H3/t9-,10-,11+,12+,13+,14?/m1/s1
InChI KeyUZMFJHRMEQGHED-XXZHWVDOSA-N
SMILESCC(=O)OCC1C(C(C2C(O1)OC(O2)(C)O)OC(=O)C)OC(=O)C
Synonyms1,2-O-(1-Methoxyethylidene)-β-D-mannopyranose Triacetate;
Canonical SMILESCC(=O)OCC1C(C(C2C(O1)OC(O2)(C)OC)OC(=O)C)OC(=O)C
Isomeric SMILESCC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]2[C@@H](O1)OC(O2)(C)OC)OC(=O)C)OC(=O)C

CAS No: 4435-05-6 Synonyms: 3,4,6-Tri-O-acetyl-1,2-O-(1-methoxyethylidene)-b-D-mannopyranose MDL No: MFCD00211213  Chemical Formula: C15H22O10 Molecular Weight: 362.33

References: 1. Carbohydr. Res. 1982, 103, 15

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