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78153-79-4 , b-2,3,4,6-Tetra-O-benzyl-D-glucopyranosyl fluoride, CAS:78153-79-4

78153-79-4 ,b-2,3,4,6-Tetra-O-benzyl-D-glucopyranosyl fluoride,
CAS:78153-79-4
C34H35FO5 / 542.64
MFCD01862264

2,3,4,6-Tetra-O-benzyl-b-D-glucopyranosyl Fluoride

b-氟代-2,3,4,6-四-O-苄基-D-吡喃葡萄糖,

2,3,4,6-Tetra-O-benzyl-b-D-glucopyranosyl Fluoride (TBG) is a drug that has antibiotic properties. It inhibits bacterial growth by binding to the D-glucose residue in the cell wall of gram positive bacteria, which prevents the synthesis of peptidoglycan and thus inhibits protein synthesis. TBG binds to the hydroxyl group on the stannic chloride to form an insoluble complex. The stannic chloride is then converted into a soluble complex with fluoride ion. TBG can be used as an antibiotic for gram positive bacteria such as Staphylococcus aureus and Streptococcus pyogenes.

2,3,4,6-Tetra-O-benzyl-beta-D-glucopyranosyl Fluoride (TBG-F) is a chemical compound belonging to the family of O-glycosides. It consists of a glucose molecule with four benzene rings attached to its hydroxyl groups and a fluorine atom attached to the anomeric carbon. TBG-F is a highly crystalline and non-hygroscopic solid with a high melting point.

TBG-F is widely used as a glycosyl donor and acceptor in organic chemistry, and it has also found applications in carbohydrate-based drug design, vaccine development, and bioconjugation. Additionally, TBG-F has shown promising results in medical imaging and diagnostic tools due to its high bioavailability and stability in biological fluids.

Synthesis and Characterization:

TBG-F is typically synthesized using a series of chemical reactions starting from commercially available starting materials. The most common synthetic strategy involves protecting the hydroxyl groups of glucose with benzyl groups, followed by the introduction of the fluorine atom to the anomeric carbon using a fluorinating agent such as Selectfluor. The final deprotection step involves the removal of the benzyl groups using hydrogenolysis or acid-catalyzed hydrolysis.

The purity and identity of TBG-F can be confirmed by various analytical techniques, including nuclear magnetic resonance (NMR), mass spectrometry (MS), infrared spectroscopy (IR), and X-ray crystallography.

Analytical Methods:

TBG-F can be quantified using various chromatographic techniques, including high-performance liquid chromatography (HPLC), gas chromatography (GC), and thin-layer chromatography (TLC). Additionally, nuclear magnetic resonance (NMR) spectroscopy can be used to analyze the structure and purity of TBG-F.

Biological Properties:

TBG-F has shown promising results in various biological applications, including drug design, vaccine development, and bioconjugation. Its high bioavailability and stability in biological fluids make it an excellent candidate for these applications.

Toxicity and Safety in Scientific Experiments:

While TBG-F has not been extensively studied for its toxicity, several studies have shown that it is relatively non-toxic in animal models. However, caution should be exercised when handling the compound due to its potential to cause eye and skin irritation.

Applications in Scientific Experiments:

TBG-F has a wide range of applications in scientific research, including organic chemistry, drug design, vaccine development, and bioconjugation. It has also been used in medical imaging and diagnostic tools due to its high bioavailability and stability in biological fluids.

Current State of Research:

Research on TBG-F is ongoing, with many studies focused on developing new synthetic strategies for its preparation and exploring its applications in various fields. Recent studies have also investigated the potential use of TBG-F in targeted drug delivery and as a biosensor for carbohydrate detection.

Potential Implications in Various Fields of Research and Industry:

The potential implications of TBG-F in various fields of research and industry are vast. Its applications range from organic chemistry to medical imaging, and it has been shown to be a useful tool in the development of drugs, vaccines, and diagnostic tools. TBG-F's unique properties make it an attractive candidate for many applications, and further research into its potential is warranted.

Limitations and Future Directions:

While TBG-F has shown great promise in various fields, there are some limitations to its use. The compound can be challenging to synthesize, and its low water solubility can be problematic in biological applications. Future directions for research could include developing new synthetic strategies to improve yields and exploring ways to enhance TBG-F's solubility in water. Additionally, studies on the compound's toxicity and safety in humans are needed before it can be widely adopted in clinical applications.

In conclusion, 2,3,4,6-Tetra-O-benzyl-beta-D-glucopyranosyl Fluoride is a valuable tool in scientific research with a wide range of applications. While there are some limitations to its use, further research into its potential is warranted, and it is an exciting area of study for scientists in many fields.

CAS Number78153-79-4
Product Name2,3,4,6-Tetra-O-benzyl-beta-D-glucopyranosyl Fluoride
IUPAC Name(2S,3R,4S,5R,6R)-2-fluoro-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
Molecular FormulaC34H35FO5
Molecular Weight542.64 g/mol
InChIInChI=1S/C34H35FO5/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 KeyQNXIKNZDQVSBCO-BGSSSCFASA-N
SMILESC1=CC=C(C=C1)COCC2C(C(C(C(O2)F)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
Canonical SMILESC1=CC=C(C=C1)COCC2C(C(C(C(O2)F)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)F)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5


CAS No: 78153-79-4 MDL No: MFCD01862264 Chemical Formula: C34H35FO5 Molecular Weight: 542.64


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