Methyl tetra-O-acetyl-β-D-glucopyranuronate

Methyl tetra-O-acetyl-β-D-glucopyranuronate

Methyl tetra-O-acetyl-β-D-glucopyranuronate (CAS No. 7355-18-2) is an acetylated derivative of β-D-glucopyranuronic acid, widely used in organic synthesis and carbohydrate chemistry. This compound is characterized by its multiple acetyl groups, which enhance its stability and reactivity.

Chemical and Physical Properties

• CAS Number: 7355-18-2
• MDL Number: MFCD00069834
• EINECS: Not specified
• Molecular Formula: C₁₅H₂₀O₁₁
• Molecular Weight: 376.31 g/mol
• Boiling Point: 412.3 ± 45.0 °C
• Melting Point: 179 °C
• Flash Point: 178.4 °C
• Density: 1.33 ± 0.1 g/cm³
• Appearance: Typically appears as a white to off-white solid

Structure and Composition

Methyl tetra-O-acetyl-β-D-glucopyranuronate features a glucopyranuronic acid backbone with four acetyl groups attached, which significantly influence its solubility and reactivity in various chemical reactions.

Biological Activity and Applications

1. Organic Synthesis: This compound is primarily used as an intermediate in the synthesis of glycosides and other carbohydrate derivatives, facilitating studies in carbohydrate chemistry.
2. Research Applications: It is utilized in biochemical research for the synthesis of complex carbohydrates and in studies related to enzyme interactions.
3. Potential Pharmaceutical Uses: Due to its structural characteristics, it may have applications in drug development, particularly in the design of glycosylated compounds.

Synthesis Methods

The compound is synthesized through the acetylation of β-D-glucopyranuronic acid, typically using acetic anhydride or acetyl chloride in the presence of a base. This process is followed by purification steps to isolate the desired product with high purity.

Safety and Handling

While generally considered safe for laboratory use, standard laboratory safety protocols should be followed to prevent exposure to skin or eyes.

Storage Recommendations

For long-term stability, the compound should be stored at temperatures between 2–8°C in a cool, dry place away from light.

In summary, methyl tetra-O-acetyl-β-D-glucopyranuronate is an important compound in organic synthesis with applications in carbohydrate chemistry and potential pharmaceutical development.

Citations:

1. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4326078.htm
2. https://pubchem.ncbi.nlm.nih.gov/compound/Methyl-1_2_3_4-tetra-O-acetyl-D-glucopyranuronate
3. https://www.avantorsciences.com/us/en/product/9566514/methyl-1-2-3-4-tetra-o-acetyl-beta-d-glucuronate-96-0
4. https://pubchem.ncbi.nlm.nih.gov/compound/95087
5. https://www.sigmaaldrich.com/IN/en/product/sigma/m5890
6. https://www.tcichemicals.com/IN/en/p/M1868
7. https://file.medchemexpress.com/batch_PDF/HY-W008523/Methyl-tetra-O-acetyl-%CE%B2-D-glucopyranuronate-COA-732836-MedChemExpress.pdf
8. https://commonchemistry.cas.org/detail