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

1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-D-galactopyranose is a chemically modified sugar derivative where the hydroxyl groups at positions 1, 2, 4, and 6 of the D-galactopyranose ring are acetylated, and the hydroxyl group at position 3 is replaced by an azido group (-N3). This compound appears as a white crystalline solid and is widely used in synthetic carbohydrate chemistry and glycobiology for producing glycosyl azides, which serve as key intermediates in the synthesis of complex glycoconjugates and glycomimetics. Its unique azido functional group is versatile for bio-orthogonal “click” chemistry, enabling the conjugation of sugars with various biomolecules for biomedical and drug discovery applications. This tetraacetylated azido sugar is also valuable in studying carbohydrate-protein interactions and developing novel therapeutic agents. It is supplied with high purity, verified by NMR, and must be stored at low temperatures (0 to -20 °C) to maintain stability.

IUPAC Name

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

Appearance

• White crystalline solid

Source

• Chemically synthesized from D-galactose derivatives by acetylation and substitution to introduce azido group at C3

Molecular Weight and Structure

• Molecular Formula: C14H19N3O9
• Molecular Weight: 373.32 g/mol
• Structure: Acetylated pyranose ring of D-galactose with azido substituent at C3; multiple acetyl groups substitute hydroxyls at 1,2,4,6 positions
• SMILES: C(C)(=O)OC[C@H]1OC(C@@HOC(C)=O)OC(C)=O

Sugar Specificity

• Derivative of D-galactose with modification at the 3 position (azido) and acetylation of other hydroxyls
• Useful as a biochemical tool to explore galactose-related glycosylation and protein recognition

Biological Activity

• Used extensively in carbohydrate synthesis to create azido sugars for click chemistry applications
• Enables conjugation and bio-orthogonal labeling of glycans, glycoproteins, and glycolipids
• Facilitates development of tools for investigating carbohydrate-binding proteins and potential therapeutics

Purity and Microbial Contamination

• Purity: ≥98% typically assured through 1H-NMR and HPLC
• Supplied chemically pure with negligible microbial contamination due to synthesis and purification protocols

Identity and Quality Control

• Confirmed by NMR, mass spectrometry, and chromatographic purity assessments
• Certification with COA and SDS available for each batch
• Melting point approximately 118–120 °C

Shelf Life and Storage

• Store at 0 to -20 °C to maintain compound stability
• Protect from moisture and heat
• Shelf life generally extends to multiple years if stored under recommended conditions

Application

• Key intermediate in glycoscience for the synthesis of azido-containing oligosaccharides and glycoconjugates
• Facilitates bio-orthogonal conjugation (click chemistry) for labeling and drug delivery applications
• Used in research for carbohydrate-protein interaction analysis and glyco-engineering
• Supports development of novel diagnostics and therapeutic agents targeting glycans

Key Characteristics

• Tetra-O-acetylated 3-azido derivative of D-galactopyranose
• CAS number 155417-78-0
• Molecular weight 373.32 g/mol, white crystalline solid
• High purity (>98%) with verified NMR spectral data
• Stable under refrigerated storage conditions
• Central role in synthetic carbohydrate chemistry and bio-orthogonal labeling
• Enables design of targeted glycoconjugate therapeutics and diagnostics
• Extensive quality control with COA and SDS provided

Citations

• Synthose 1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-D-galactopyranose
• ChemicalBook detailed data
• BOC Sciences catalog
• CymitQuimica data and ordering info
• PubChem 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose
• TCI Chemicals 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-α-D-galactopyranose
• Sigma-Aldrich acetylated sugar derivatives
• Google Patents synthesis methods
• MedChemExpress related azido sugar standards
• Glentham Life Sciences acetylated azido sugars