1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-β-D-galactopyranose

1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-β-D-galactopyranose is a chemically synthesized carbohydrate derivative derived from D-galactose. This compound features acetylation at the 1st, 3rd, 4th, and 6th hydroxyl groups of the galactopyranose ring, while the hydroxyl group at the 2nd position is replaced by an azido (-N3) functional group. It presents as a white crystalline solid with significant utility in carbohydrate chemistry due to the azido group’s reactivity, which enables its use in bioorthogonal click chemistry for conjugation and labeling purposes. Researchers use this compound as an intermediate for constructing glycomimetics, glycoconjugates, and complex oligosaccharides, facilitating the study of carbohydrate-protein interactions and enzymatic recognition. With its established stability and high purity, 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-β-D-galactopyranose is critical for therapeutic development, diagnostics, and chemical biology research.

IUPAC Name

• (2S,3R,4S,5R,6R)-3,5,6-triacetyloxy-4-azidooxan-2-yl methyl acetate

Appearance

• White crystalline powder

Source

• Synthetic product via chemical acetylation and azido substitution of D-galactose derivatives

Molecular Weight and Structure

• Molecular Formula: C14H18N3O9
• Molecular Weight: 375.31 g/mol
• Structure: Acetylated β-D-galactopyranose ring with azido substitution at C2 and acetyl groups at 1,3,4,6 positions
• SMILES: CC(=O)OC[C@@H]1OC(OC(C)=O)C@HC@@HO[C@@H]1OC(C)=O

Sugar Specificity

• β-Glycoside derivative of D-galactose, modified with azido functionality
• Serves as key synthetic intermediate in galactose-related glycosylation and glycomimetic chemistry

Biological Activity

• Useful in click chemistry applications for conjugation of sugars to biomolecules
• Enables exploration of glycan interactions and enzyme specificities in biological systems
• Facilitates development of drug candidates and diagnostics involving glycan recognition

Purity and Microbial Contamination

• Purity ≥98% as confirmed by NMR, HPLC, and/or GC analysis
• Chemically pure with negligible microbial contamination due to synthetic preparation and rigor in QC standards

Identity and Quality Control

• Identity confirmed by nuclear magnetic resonance spectroscopy, mass spectrometry, and chromatographic purity profiling
• Supplied with Certificates of Analysis and material safety data sheets (SDS)
• Melting point range approximately 120-125 °C

Shelf Life and Storage

• Store in well-sealed containers at 0 to -20 °C, protected from moisture and light
• Stable for up to 2 years if stored properly

Application

• Intermediate for synthesis of azido-tagged glycans used in bioorthogonal click chemistry
• Employed in biochemical and medicinal chemistry research for studying carbohydrate function
• Facilitates creation of glycoconjugates for use in diagnostics, therapeutics, and biochemical assays
• Supports enzymatic evaluation and glycomimetic development

Key Characteristics

• Acetylated azido-substituted β-D-galactopyranose derivative
• CAS number: 1158970-33-2
• Molecular weight 375.31 g/mol; white crystalline powder
• High chemical purity, fully characterized spectral profiles
• Stable when stored refrigerated and protected from light/moisture
• Valuable for click chemistry, glycosylation studies, and drug development
• Supplied with comprehensive quality documentation

Citations

• MedChemExpress 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-β-D-galactopyranose
• Synthose azido sugar compounds
• PubChem molecular data
• Google Patents synthetic methods
• ChemicalBook detailed compound listing
• Sigma-Aldrich acetylated sugar derivatives
• TCI Chemicals carbohydrate/deoxy sugar derivatives
• CymitQuimica azide sugar catalog
• Glentham azido sugar product
• BOC Sciences acetylated azido carbohydrate intermediates