2,3,4,6-Tetra-O-acetyl-a-D-glucopyranosyl bromide, Acetobrom glucose

2,3,4,6-Tetra-O-acetyl-a-D-glucopyranosyl bromide, Acetobrom glucose

2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl bromide (Acetobrom glucose, CAS No: 572-09-8) is a highly specialized glycosyl donor widely used in carbohydrate and organic synthesis, especially for the formation of β-glucosides and complex oligosaccharides.chemicalbook+2

Chemical Identity and Properties

• IUPAC Name: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate.pubchem.ncbi.nlm.nih+1

• Molecular Formula: C₁₄H₁₉BrO₉.simsonpharma+2

• Molecular Weight: 411.2 g/mol.fluorochem+2

• Physical State: White to light yellow powder or crystalline solid.tcichemicals+1

• Purity: Typically ≥98%, with stabilization using 1–2% CaCO₃ to prevent decomposition.pubchem.ncbi.nlm.nih+1

• Melting Point: 87–92 °C.tcichemicals

• Optical Rotation: [α]D20=+192[α]^{20}_D = +192[α]D20=+192 to $+205°$ (C=3, in CHCl₃).tcichemicals

• Storage: Store frozen (<0°C), under inert gas, protected from light, moisture, and heat.chemicalbook+1

Analytical and Safety Notes

• Purification: Recrystallization from ether/pentane and drying under vacuum are recommended for analytical grade use; product is sensitive to moisture and light.chemicalbook

• Hazards: May cause skin, eye, and respiratory irritation (GHS07, hazard codes H315-H319-H335); use protective equipment and avoid inhalation or direct contact.chemicalbook

• Stabilization: Solutions and solids are stabilized with CaCO₃ to increase shelf-life and maintain high purity.pubchem.ncbi.nlm.nih+1

Applications and Uses

• Synthetic Intermediate: Essential for the synthesis of β-glucosides, glycosylated pharmaceuticals, and macromolecular conjugates.bocsci+1

• Industrial Use: Employed as a modifying agent for biomaterials such as poly(ethylene terephthalate), improving blood compatibility and surface properties.chemicalbook

• Research: Used in antiviral drug development, including as a precursor or reagent in oseltamivir synthesis.bocsci

• General: Finds applications in medicinal chemistry, diagnostic reagent production, and carbohydrate assembly studies.bocsci+1

Synonyms and Registry Data

• Synonyms: Acetobromo-α-D-glucose, Acetobromglucose, Tetraacetyl bromoglucose, α-D-glucopyranosyl bromide tetraacetate.pharmaffiliates+2

• CAS No.: 572-09-8.simsonpharma+2

• MDL Number: MFCD00063254.pubchem.ncbi.nlm.nih+1

Industry and Research Implications

• This compound is a mainstay in carbohydrate chemistry and glycoscience, critical for high-yield, selective glycosylation.bocsci+1

• Ongoing research focuses on enhancing stability, broadening applications in drug delivery systems, and optimizing its role in the synthesis of glycoside derivatives for pharmaceutical development.bocsci+1

2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl bromide remains indispensable for synthetic biochemistry and industrial glycosylation reactions in advanced research and manufacturing.pubchem.ncbi.nlm.nih+2