[(2R,3R,4S,5R,6R)-3,4,5-tris (acetyloxy)-6-bromooxan-2-yl]methyl acetate

 [(2R,3R,4S,5R,6R)-3,4,5-tris (acetyloxy)-6-bromooxan-2-yl]methyl acetate

[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate, commonly referred to as 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide, is a brominated carbohydrate derivative that serves as a versatile reagent in organic synthesis and carbohydrate chemistry.

Chemical Properties

• CAS Number: 572-09-8
• MDL No.: MFCD00063254
• Catalog Number: A831344
• EINECS: Not available
• Molecular Formula: C₁₄H₁₉BrO₉
• Molecular Weight: 411.20 g/mol
• Boiling Point: 412 °C at 760 mmHg
• Melting Point: 87.0 to 92.0 °C
• Flash Point: 412 °C at 760 mmHg
• Density: 1.49 g/cm³
• Appearance: White powder
• Storage Conditions: Store at 2–8 °C for long-term stability (months).

Physical Characteristics

This compound is characterized by its white powder appearance and significant thermal stability, indicated by its high boiling and melting points. The density of approximately 1.49 g/cm³ suggests it is relatively dense compared to many organic compounds.

Applications

1. Organic Synthesis:
   • [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate is utilized as a glycosylating agent in the synthesis of various glycosides and oligosaccharides.
2. Biochemical Research:
   • It serves as a biochemical reagent for studying carbohydrate interactions and enzyme activities related to glycosylation processes.
3. Pharmaceutical Development:
   • The compound can be used in the synthesis of biologically active compounds and potential drug candidates that require specific glycosylation patterns for activity.
4. Analytical Chemistry:
   • Employed in analytical methods to identify and quantify carbohydrates in complex mixtures.

Mechanism of Action

The bromine atom in this compound enhances its electrophilicity, making it a good substrate for nucleophilic attack by alcohols or other nucleophiles during glycosylation reactions. This property is crucial for forming glycosidic bonds in carbohydrate chemistry.

Safety Profile

While specific safety data may be limited for this compound, standard laboratory safety practices should be followed when handling it. Personal protective equipment (PPE) such as gloves and goggles should be used to minimize exposure.

Conclusion

[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate (CAS No. 572-09-8) is an important reagent in organic synthesis and carbohydrate chemistry. Its unique properties make it valuable for applications in biochemical research and pharmaceutical development.

Citations:

1. https://www.chemsrc.com/en/cas/572-09-8_685140.html
2. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9142437.htm
3. https://pubchem.ncbi.nlm.nih.gov/compound/Acetobromglucose
4. https://www.tcichemicals.com/IN/en/p/T1961
5. https://www.sigmaaldrich.com/US/en/search/572-09-8?focus=products&page=1&perpage=30&sort=relevance&term=572-09-8&type=cas_number
6. https://www.bldpharm.com/products/572-09-8.html
7. https://www.chemicalbook.com/CASEN_572-09-8.htm
8. https://www.ottokemi.com/carbohydrates-a-to-z/a-4235.aspx