2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl bromide, Acetobrom galactose

2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl bromide, Acetobrom galactose

2,3,4,6-Tetra-O-acetyl-α-D-galactopyranosyl bromide (Acetobrom galactose, CAS No: 3068-32-4) is a specialized organic compound commonly used as a glycosyl donor in organic synthesis, notably for constructing complex oligosaccharides and glycoproteins in both research and industrial settings.discofinechem+1

Chemical Identity and Properties

• IUPAC Name: (3,4,5-triacetyloxy-6-bromooxan-2-yl)methyl acetate.fluorochem+1

• Molecular Formula: C₁₄H₁₉BrO₉.chemicalbook+2

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

• Appearance: White crystalline solid when pure.synthose+1

• Storage: Highly sensitive to temperature and moisture, typically stabilized with 2% CaCO₃ and stored in a freezer to prevent degradation.pubchem.ncbi.nlm.nih+2

• SMILES: CC(=O)OCC1C(C(C(C(O1)Br)OC(=O)C)OC(=O)C)OC(=O)C.fluorochem+1

Physical and Analytical Characterization

• Purification involves standard organic protocols, with free-flowing chloroform extraction and drying, followed by ether/petroleum crystallization for high purity.chemicalbook

• Structure confirmed via NMR, IR, MS, and HPLC analytical methods for quality control and research applications.chemsynlab

Applications

• Role as Reagent: Key glycosyl donor for Koenigs-Knorr and related galactosylation reactions, facilitating the synthesis of galactosylated molecules, spacer-equipped phosphorylated saccharide fragments, and other critical carbohydrate derivatives in biochemistry.sigmaaldrich+2

• Research Use: Widely leveraged for building blocks in complex oligosaccharide and glycoprotein synthesis, including drug delivery systems and novel anticancer agents.chemsynlab

Biological and Safety Notes

• Displays documented anti-inflammatory and potential anti-tumor properties in exploratory studies, though not intended for pharmaceutical use without further validation.chemsynlab

• Generally low toxicity, but direct contact may cause skin or eye irritation—appropriate laboratory safety protocols (gloves, eye protection) are essential.chemsynlab

• Low water solubility can limit certain applications, leading to ongoing research for more soluble derivatives.chemsynlab

Synonyms and Registry Data

• Synonyms: Acetobromo-α-D-Galactose, Acetobromogalactose, α-D-Galactopyranosyl bromide tetraacetate.tcichemicals+3

• CAS No.: 3068-32-4.chemicalbook+1

Industry and Research Implications

• Used extensively in carbohydrate chemistry, biomedical research, and the development of bioconjugates and designer oligosaccharides for diagnostics and therapeutics.chemsynlab

• Future research centers on improving synthesis yield, solubility enhancements, and expanding applicability in drug discovery and delivery systems.chemsynlab

This compound serves as a crucial enabling reagent for galactosylation reactions, supporting advancements in glycoscience and biomolecular engineering.discofinechem+2