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  • 25320-59-6 , 四苄基-α-D-氯代葡萄糖, CAS: 25320-59-6
25320-59-6 , 四苄基-α-D-氯代葡萄糖, CAS: 25320-59-6

25320-59-6 , 四苄基-α-D-氯代葡萄糖, CAS: 25320-59-6

25320-59-6 , 四苄基-α-D-氯代葡萄糖,
Tetra-O-benzyl-a-D-glucopyranosyl chloride ,
CAS: 25320-59-6
C34H35ClO5 / 559.09

Tetra-O-benzyl-a-D-glucopyranosyl chloride

四苄基-α-D-氯代葡萄糖,

2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl chloride (TBGC) is a molecule of interest in organic chemistry. This molecule belongs to the class of carbohydrates and is used as a starting material for the synthesis of specific oligosaccharides. So far, TBGC has shown a promising ability to produce a variety of oligosaccharides with biological functions, attracting attention from various fields of research. In this paper, we will describe the properties of TBGC, including its physical and chemical properties, synthesis, characterization, and analytical methods. The paper also discusses the biological properties, toxicity, safety in scientific experiments, and potential applications in various fields of research and industry. We also highlight the current state of research focusing on TBGC and its future directions.

Synthesis and Characterization:

TBGC can be synthesized by the reaction of glucose with benzyl chloride in the presence of a base such as potassium carbonate. The produced benzylated glucose derivative is then treated with thionyl chloride to obtain TBGC. TBGC can be characterized through various methods such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and high-performance liquid chromatography (HPLC).

Analytical Methods:

NMR spectroscopy is a powerful analytical tool used to identify and characterize various compounds, including TBGC. The NMR spectrum of TBGC shows characteristic peaks corresponding to its chemical structure. HPLC is another analytical technique used to separate and quantify different compounds, including TBGC.

Biological Properties:

TBGC has been shown to possess biological properties such as anti-inflammatory, anti-viral, and anti-tumor activities. These properties result from the glycosylation of TBGC to form oligosaccharides that exhibit these functions. In a recent study, a TBGC derivative was glycosylated to form an oligosaccharide with potent anti-tumor activity.

Toxicity and Safety in Scientific Experiments:

TBGC has not been reported to be toxic in scientific experiments. However, as with any chemical, it is essential to take the necessary precautions when handling TBGC.

Applications in Scientific Experiments:

TBGC has been used as a starting material for the synthesis of specific oligosaccharides with biological functions. These oligosaccharides have potential applications in various fields such as drug development, food and beverage industries, and agriculture.

Current State of Research:

TBGC's use as a glycosyl donor has attracted considerable research attention in recent years, resulting in the discovery of various oligosaccharides with specific biological functions. Researchers are currently exploring new strategies to optimize the synthesis and characterization of TBGC and its derivatives. The use of TBGC in drug development is a rapidly growing area of research, further highlighting the compound's potential.

Future Directions:

1. Optimization of Glycosylation Reactions: Explore new reaction conditions and catalysts to improve the yield and selectivity of TBGC glycosylation reactions.

2. Modified TBGC Derivatives: Exploration of new TBGC derivatives and how they affect the resulting oligosaccharide structures and biological activities.

3. Industrial Application ofTBGC: Investigate TBGC's potential as an industrial starter material for the production of specific oligosaccharides, with applications in food, agriculture, and biomedical industries.

4. Mechanisms of Action: Investigate the mechanisms underlying the biological activities of TBGC-derived oligosaccharides to understand their therapeutic potential.

5. TBGC in Combination Therapy: Explore the potential of TBGC-derived oligosaccharides in combination therapy with other drugs or therapies.

6. TBGC in Nanoparticles: Exploration of TBGC's potential to be incorporated into nanoparticles for drug delivery and medical imaging purposes.

7. TBGC in Vaccines: Investigate the potential of TBGC-derived oligosaccharides in the development of vaccines against various diseases.

8. Glycoengineering: Investigate how TBGC-derived oligosaccharides can be modified using glycoengineering to achieve specific functions such as improved immunogenicity or enhanced therapeutic effects.

9. Enzymatic Glycosylation: Explore the use of enzymes in TBGC glycosylation reactions to improve yield and selectivity while reducing the use of hazardous reagents.

10. Safety and Toxicity: Further research into the safety and toxicity of TBGC and its derivatives to optimize safety precautions when handling them.

CAS Number25320-59-6
Product Name2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl chloride
IUPAC Name(2R,3R,4S,5R,6R)-2-chloro-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
Molecular FormulaC34H35ClO5
Molecular Weight559.09 g/mol
InChIInChI=1S/C34H35ClO5/c35-34-33(39-24-29-19-11-4-12-20-29)32(38-23-28-17-9-3-10-18-28)31(37-22-27-15-7-2-8-16-27)30(40-34)25-36-21-26-13-5-1-6-14-26/h1-20,30-34H,21-25H2/t30-,31-,32+,33-,34+/m1/s1
InChI KeyPCQHHGZMQLZGQM-RUOAZZEASA-N
SMILESC1=CC=C(C=C1)COCC2C(C(C(C(O2)Cl)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
Synonyms2,3,4,6-Tetrakis-O-(phenylmethyl)-α-D-glucopyranosyl Chloride;
Canonical SMILESC1=CC=C(C=C1)COCC2C(C(C(C(O2)Cl)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
Isomeric SMILESC1=CC=C(C=C1)COC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)Cl)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5


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