2,3,6,2′,3′,4′,6′-Hepta-O-acetyl-α-D-lactosyl bromide, Acetobrom lactose

2,3,6,2′,3′,4′,6′-Hepta-O-acetyl-α-D-lactosyl bromide, Acetobrom lactose

2,3,6,2′,3′,4′,6′-Hepta-O-acetyl-α-D-lactosyl bromide (Acetobrom lactose, CAS No: 4753-07-5) is a highly acetylated, brominated lactose derivative, used in advanced carbohydrate chemistry as a glycosyl donor for the synthesis of complex oligosaccharides and glycoconjugates.chemicalbook

Chemical Identity and Properties

• IUPAC Name / Structure:
  Often referenced as bromo heptaacetyl-D-lactoside or acetobromo-α-D-lactose; structurally, it is a lactose (galactosyl-glucose disaccharide) tetraacetylated on the galactose and triacetylated on the glucose part, with a bromine substituent for activation.chemicalbook

• Molecular Formula: C₂₆H₃₅BrO₁₇.chemicalbook

• Molecular Weight: 699.45 g/mol.chemicalbook

• Physical State: White to off-white powder.chemicalbook

• Melting Point: 140–141°C.chemicalbook

• Density: 1.47 ± 0.1 g/cm³ (predicted).chemicalbook

Storage and Stability

• Storage Conditions:
  Requires storage in a −20°C freezer, under inert atmosphere; highly moisture and temperature sensitive, and notably hygroscopic.chemicalbook

• Stability:
  Sensitive to moisture, temperature, and air; for best results, store with desiccant and work quickly under dry, cold conditions.chemicalbook

Solubility and Handling

• Solubility: Soluble in chloroform.chemicalbook

• Handling: Careful handling needed due to hygroscopic nature; utilizes CaCO₃ for stabilization.chemicalbook

Applications

• Synthetic Role: Used extensively as a glycosyl donor in Koenigs-Knorr-type reactions for the synthesis of lactosides, designer oligosaccharides, and various lactose-based bioconjugates for research in glycoscience and pharmaceuticals.chemicalbook

• Research Importance: Serves as a protected intermediate for the stepwise synthesis of longer carbohydrate chains, modification of surfaces with lactose-derived ligands, and studies in biological recognition.chemicalbook

Synonyms and Registry Data

• Synonyms: Acetobromo-α-D-lactose, Heptaacetyl lactosyl bromide, Acetobromo lactoside.chemicalbook

• CAS No: 4753-07-5.chemicalbook

Research and Industrial Value

This compound is essential in synthetic carbohydrate chemistry, enabling the formation of well-defined oligosaccharides and glycosylated molecules for use in immunology, cell biology, and material functionalization.chemicalbook

2,3,6,2′,3′,4′,6′-Hepta-O-acetyl-α-D-lactosyl bromide remains a specialist reagent for glycosylation reactions, especially in the construction of biologically active saccharide structures.chemicalbook