beta-D-Glucose pentaacetate
[CAS# 604-69-3]

Identification

• Classification: Biochemical >> Carbohydrate >> Monosaccharide
• Name: beta-D-Glucose pentaacetate
• Synonyms: 1,2,3,4,6-Penta-O-acetyl-beta-D-glucopyranose; Acetyl 2,3,4,6-tetra-o-acetyl-beta-D-glucopyranoside
• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.34
• CAS Registry Number: 604-69-3
• EC Number: 210-074-8
• SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Melting point: 130 - 132 ºC (Expl.)
• Boiling point: 434.8±45.0 ºC 760 mmHg (Calc.)^*
• Flash point: 188.1±28.8 ºC (Calc.)^*
• Index of refraction: 1.482 (Calc.)^*
• Alpha: 5 º (c=1, CHCl3) (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

β--D-Glucose pentaacetate is a fully acetylated derivative of the monosaccharide glucose in which all five hydroxyl groups are converted to acetate esters. Its molecular formula is C₁₄H₂₀O₁₀, with a molecular weight of approximately 356.31 g/mol. The compound retains the β-anomeric configuration at the anomeric carbon, preserving the stereochemistry of D-glucose while the acetyl groups increase hydrophobicity and chemical stability. Acetylation protects the hydroxyl groups, making the molecule a versatile intermediate in carbohydrate chemistry.

The synthesis of β-D-glucose pentaacetate typically involves the reaction of D-glucose with acetic anhydride in the presence of an acid catalyst, such as sulfuric acid or pyridine. The reaction proceeds through acetylation of each hydroxyl group, with the anomeric center favoring the β--configuration due to thermodynamic and stereoelectronic effects. Reaction conditions are optimized to ensure complete acetylation and to minimize formation of side products, such as partial acetates or α-anomer derivatives. Purification is generally achieved by recrystallization or chromatographic techniques.

Chemically, β--D-glucose pentaacetate is relatively stable compared with free glucose due to the protection of hydroxyl groups. The acetate esters can undergo selective hydrolysis under acidic or basic conditions to yield partially or fully deprotected glucose derivatives. The anomeric acetate is particularly reactive and can participate in glycosylation reactions, serving as a donor in the synthesis of oligosaccharides, glycosides, and other carbohydrate-based conjugates. The molecule’s stereochemistry and ester functionality provide both reactivity and selectivity in synthetic transformations.

Physically, β--D-glucose pentaacetate is typically a crystalline solid at room temperature and is soluble in organic solvents such as dichloromethane, chloroform, and ethanol, while exhibiting limited solubility in water. The compound is chemically stable under dry, neutral conditions, but hydrolyzes in the presence of moisture or strong acids/bases, releasing acetic acid. Its crystalline nature and defined stereochemistry facilitate handling, storage, and use in synthetic applications.

In practical applications, β--D-glucose pentaacetate is widely used as a protected glucose intermediate in carbohydrate synthesis, glycosylation reactions, and the preparation of glycosyl donors. It is employed in the synthesis of oligosaccharides, nucleoside analogues, glycoprotein mimics, and other biologically relevant molecules. The anomeric β-configuration allows selective reactions at the anomeric position, enabling the controlled construction of glycosidic bonds and stereochemically defined carbohydrates.

Overall, β--D-glucose pentaacetate is a fully acetylated glucose derivative combining stereochemical fidelity, protected hydroxyl groups, and an anomerically reactive site. Its chemical stability, solubility in organic solvents, and versatile reactivity make it an essential intermediate for synthetic carbohydrate chemistry and the preparation of functionalized sugar derivatives.

References

2022. Amines-mediated �-glucose pentaacetate to generate photoluminescent polymer-carbon nanodots for visual monitoring the freshness of shrimp. Talanta.
DOI: 10.1016/j.talanta.2022.123706