Tetra-o-benzoyl-D-xylofuranose

Tetra-o-benzoyl-D-xylofuranose

Tetra-o-benzoyl-D-xylofuranose (CAS No. 5432-87-1) is a glycosylated compound that plays a crucial role in carbohydrate chemistry and biochemical research. This compound is characterized by its four benzoyl groups, which enhance its stability and reactivity, making it a valuable reagent in the synthesis of complex carbohydrates and nucleosides.

Chemical Properties

• CAS Number: 5432-87-1
• MDL Number: MFCD00037898
• EINECS: Not available
• Molecular Formula: C33H26O9
• Molecular Weight: 566.55 g/mol
• Boiling Point: 688.2 ± 55.0 °C (predicted)
• Melting Point: 165-166 °C

Structure and Composition

Tetra-o-benzoyl-D-xylofuranose features a xylofuranose backbone with four benzoyl groups attached at the hydroxyl positions. Key structural features include:

1. Benzoyl Groups: The presence of these aromatic acyl groups enhances the compound’s solubility and stability, making it suitable for various chemical reactions.
2. Furanose Structure: The five-membered furanose ring is essential for biological recognition processes, allowing the compound to interact with enzymes and other biomolecules.
3. Hydroxyl Groups: The remaining hydroxyl groups contribute to the compound’s reactivity and ability to participate in glycosylation reactions.

Applications

Tetra-o-benzoyl-D-xylofuranose is widely used in several applications:

Biochemical Research

1. Glycosylation Reactions: This compound acts as a glycosyl donor in the synthesis of oligosaccharides and glycoconjugates, facilitating the transfer of glycosyl groups to acceptor molecules.
2. Enzymatic Studies: It serves as a substrate for glycosyltransferases, enzymes that catalyze the formation of glycosidic bonds, allowing researchers to study enzyme kinetics and carbohydrate metabolism.

Pharmaceutical Development

1. Drug Design: Its unique structure makes it a candidate for developing glycosylated drugs that require specific targeting mechanisms or enhanced bioactivity.
2. Prodrug Formulation: The compound can be explored for its potential in drug conjugation, improving the effectiveness and selectivity of therapeutic agents.

Chemical Synthesis

1. Intermediate in Synthesis: Tetra-o-benzoyl-D-xylofuranose is used as an intermediate in the synthesis of more complex carbohydrate derivatives and nucleosides.

Safety and Handling

While specific safety data for Tetra-o-benzoyl-D-xylofuranose are not extensively documented, standard laboratory safety practices should be followed:

1. Personal Protective Equipment (PPE): Use gloves, goggles, and lab coats when handling this compound to avoid skin or eye contact.
2. Ventilation: Work in a well-ventilated area or fume hood to minimize exposure to vapors or dust.
3. Storage Conditions: Store the compound at temperatures between 2 to 8 °C to maintain stability.
4. Disposal Guidelines: Dispose of waste according to local regulations regarding hazardous materials.

Summary

In summary, Tetra-o-benzoyl-D-xylofuranose (CAS No. 5432-87-1) is an important reagent in carbohydrate chemistry and biochemical research for studying glycosylation processes and synthesizing glycosylated compounds. Its unique structural features enable its use in drug development and enzymatic assays, making it a valuable tool for researchers in the field.

Citations:

1. https://www.benchchem.com/product/b561754
2. https://www.benchchem.com/product/b1453174
3. https://www.biosynth.com/p/MT05208/5432-87-1-1235-tetra-o-benzoyl-a-d-xylofuranose
4. https://pubchem.ncbi.nlm.nih.gov/compound/11162923
5. https://www.mdpi.com/1422-8599/2022/2/M1382
6. https://www.scbt.com/p/1-2-3-4-tetra-o-benzoyl-d-xylofuranose-5432-87-1
7. http://chemsynlab.com/en/product/30571-56-3.html
8. https://www.cphi-online.com/2-3-4-6-tetra-o-benzyl-d-galactose-prod563501.html