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6386-24-9 , Tetra-O-benzyl D-galactopyranose, CAS:6386-24-9

6386-24-9 , Tetra-O-benzyl D-galactopyranose,
CAS:6386-24-9
C34H36O6 / 540.65
MFCD00132927

2,3,4,6-Tetra-O-benzyl-D-galactopyranose

四苄基-D-半乳糖,

2,3,4,6-Tetra-O-benzyl-D-galactopyranose is an isomeric sugar that is found in a variety of natural and synthetic carbohydrates. It has been shown to inhibit glycosidase enzymes such as aminoglycoside N-acetyltransferases and α-glycosidases. The stereoselective properties of 2,3,4,6-Tetra-O-benzyl-D-galactopyranose make it a good candidate for the treatment of drug resistant bacteria. This compound has been shown to have inhibitory activity against the hydrolase family of enzymes that includes proteases, lipases, and phospholipases.

2,3,4,6-Tetra-O-benzyl-D-galactopyranose is a chemical compound that belongs to the class of carbohydrate compounds. It has been the subject of scientific research in various fields ranging from medicinal chemistry to material science. In this paper, we will provide an overview of the definition and background of this compound, its 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, and limitations and future directions.

Synthesis and Characterization:

TBG can be synthesized by the benzylidene acetalization of galactose using benzaldehyde and catalytic p-toluenesulfonic acid as a condensing agent. The synthesized TBG can then be purified using a silica gel column chromatography or recrystallization in ethanol. The purity of TBG can be determined by using HPLC or NMR spectroscopy.

Analytical Methods:

Various analytical methods can be used to characterize and analyze TBG. These include nuclear magnetic resonance (NMR) spectroscopy, high-performance liquid chromatography (HPLC), mass spectrometry, and X-ray crystallography. NMR spectroscopy can be used to determine the structure, purity, and stereochemistry of TBG. HPLC can be used to separate and quantify TBG in complex mixtures, while mass spectrometry can be used to identify the molecular weight and fragmentation pattern of TBG. X-ray crystallography can be used to determine the three-dimensional structure of TBG.

Biological Properties:

Several studies have investigated the biological properties of TBG. TBG has been shown to exhibit antiviral, antitumor, and antibacterial activities. For instance, TBG has been shown to inhibit the replication of human immunodeficiency virus type 1 (HIV-1) by blocking the fusion between viral and host cell membranes. TBG has also been shown to induce apoptosis in cancer cells by activating caspases and disrupting the mitochondrial membrane potential. In addition, TBG has been shown to inhibit the growth of various bacterial strains such as Escherichia coli and Staphylococcus aureus.

Toxicity and Safety in Scientific Experiments:

Several studies have investigated the toxicity and safety of TBG in scientific experiments. TBG has been found to be relatively non-toxic to mammalian cells and has low acute toxicity in rodents. However, long-term exposure to TBG may lead to liver or kidney damage. Therefore, caution should be exercised when handling and using TBG in scientific experiments, and proper safety precautions should be taken.

Applications in Scientific Experiments:

TBG has been used as a starting material for the synthesis of various glycoconjugates such as glycopeptides, glycolipids, and glycosylated proteins. Glycoconjugates play an important role in various biological processes such as cell-cell recognition, immune response, and signal transduction. TBG has also been used as a building block for the synthesis of dendrimers, which are highly-branched macromolecules with potential applications in drug delivery, gene therapy, and molecular imaging.

Current State of Research:

Several studies are currently underway to investigate the potential applications of TBG in various fields of research such as medicinal chemistry, nanotechnology, and material science. For instance, TBG has been used as a template for the synthesis of nanocages with potential applications in drug delivery and catalysis. TBG has also been used as a building block for the synthesis of conductive polymers with potential applications in organic electronics and sensing.

Potential Implications in Various Fields of Research and Industry:

TBG has potential implications in various fields of research and industry. In medicinal chemistry, TBG derivatives have shown promise as antiviral and anticancer agents. In nanotechnology, TBG-based dendrimers and nanocages have shown potential applications in drug delivery and catalysis. In material science, TBG-based polymers and crystals have shown potential applications in organic electronics and sensing.

Limitations and Future Directions:

Several limitations and future directions exist in the research on TBG. One limitation is the relatively low yield of TBG synthesis, which limits its use in large-scale industrial applications. Another limitation is the toxicity and safety concerns associated with TBG, which require careful handling and safety precautions. Future directions in the research on TBG include the development of more efficient and high-yielding synthesis methods, the investigation of novel TBG derivatives with improved biological and physicochemical properties, and the exploration of new applications in various fields of research and industry.

Conclusion:

In conclusion, 2,3,4,6-Tetra-O-benzyl-D-galactopyranose is a versatile compound that has been the subject of scientific research in various fields ranging from medicinal chemistry to material science. TBG exhibits unique physical and chemical properties, has potential biological activities, and has potential implications in various fields of research and industry. While several limitations and safety concerns exist, future directions in the research on TBG hold promise for the development of novel applications and improved synthetic methods.

CAS Number6386-24-9
Product Name2,3,4,6-Tetra-O-benzyl-D-galactopyranose
IUPAC Name(3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol
Molecular FormulaC34H36O6
Molecular Weight540.65 g/mol
InChIInChI=1S/C34H36O6/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/h1-20,30-35H,21-25H2/t30-,31+,32+,33-,34?/m1/s1
InChI KeyOGOMAWHSXRDAKZ-BJPULKCASA-N
SMILESC1=CC=C(C=C1)COCC2C(C(C(C(O2)O)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
Canonical SMILESC1=CC=C(C=C1)COCC2C(C(C(C(O2)O)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(O2)O)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5


CAS No: 53081-25-7,4291-69-4,6386-24-9 MDL No: MFCD00132927 Chemical Formula: C34H36O6 Molecular Weight: 540.65

COA:

Name: 2,3,4,6-Tetra-O-benzyl-D-galactopyranose 

CAS: 53081-25-7, 6386-24-9      M.F.: C34H36OM.W.: 540.65

Items

Standards

Results

Appearance

White or slightly yellow solid or syrup

Complies

Solubility

Insoluble in water, easily soluble in CHCl3

Complies

NMR and MS

Should comply

Complies

Identification

IR and HPLC

Complies

Water

Max. 0.5%

0.02%

Residue on ignition

Max. 0.5%

0.1%

TLC

Should be one spot

One spot

Assay

Min. 98%

98.4%


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