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

1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose is a chemically modified sugar derivative where the hydroxyl groups at positions 1, 3, 4, and 6 of the D-galactopyranose ring are acetylated, and the hydroxyl group at position 2 is replaced by an azido group (-N3). This compound appears as a white crystalline powder and serves as an important intermediate in synthetic carbohydrate chemistry. It is widely used in the preparation of azide-functionalized sugar derivatives, which are crucial in bio-orthogonal click chemistry for the labeling and conjugation of glycans to other biomolecules. The azido substitution enables selective and efficient chemical transformations, making it valuable in drug development, glycomimetics, and biochemical studies. This compound allows researchers to investigate carbohydrate-protein interactions, enzymatic specificities, and to synthesize complex glycoconjugates under controlled conditions. It is supplied with high purity, with detailed identity and quality control, and requires proper storage to maintain its stability for research and pharmaceutical applications.

IUPAC Name

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

Appearance

• White crystalline solid

Source

• Synthetic chemical derived from D-galactose by acetylation and azido substitution at position 2

Molecular Weight and Structure

• Molecular Formula: C14H18N3O9
• Molecular Weight: 375.31 g/mol
• Structure: Acetylated pyranose ring of D-galactose with azido substitution at carbon 2, acetyl groups at 1,3,4,6 positions
• SMILES: CC(=O)OCC1OC(OC(C)=O)C@HC@HO[C@H]1OC(C)=O

Sugar Specificity

• A 2-azido-2-deoxy derivative of D-galactose, specific for glycosylation and click chemistry applications
• Acts as a versatile intermediate to modify galactose-containing glycans

Biological Activity

• Used primarily as a synthetic precursor for bio-orthogonal labeling of glycans and glycoconjugates
• Facilitates the study of glycan-mediated biological interactions and enzyme functions
• Enables targeted drug delivery and diagnostic development through chemical conjugation techniques

Purity and Microbial Contamination

• Purity ≥98% confirmed by NMR and HPLC
• Low microbial contamination due to chemical synthesis and purification
• Supplied with Certificates of Analysis confirming quality standards

Identity and Quality Control

• Identified by comprehensive NMR, MS, and HPLC spectral analysis
• Accompanied by Certificate of Analysis and Safety Data Sheets
• Melting point ~125-127°C

Shelf Life and Storage

• Store under refrigeration at 0 to -20 °C
• Protect from moisture, heat, and light
• Stable up to 2 years when stored under recommended conditions

Application

• Key intermediate in glycoscience for preparing azido-modified sugars
• Used in click chemistry for conjugation of sugars to biomolecules
• Facilitates creation of glycoconjugates for therapeutic and diagnostic purposes
• Employed in studying carbohydrate-protein interactions and enzymatic modifications
• Suitable for drug discovery and development of targeted delivery systems

Key Characteristics

• Tetra-O-acetylated 2-azido-2-deoxy-D-galactopyranose
• CAS number: 1092317-21-1
• Molecular weight 375.31 g/mol, white crystalline powder
• High purity with verified spectral data
• Stable under proper refrigerated storage
• Essential for synthetic chemistry and biochemical glycoscience
• Enables bio-orthogonal conjugation in research and pharmaceutical development
• Quality controlled and supplied with full documentation
• Recognized intermediate in carbohydrate click chemistry reactions
• Widely applicable in glycomimetic and glycoconjugate synthesis

Citations

• PubChem entry, 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose
• Synthose product info, acetylated azido sugars
• Google Patents on azido-D-galactopyranose synthesis
• ChemicalBook acetylated azido sugars
• MedChemExpress azido sugar standards
• Sigma-Aldrich acetyl sugar derivatives
• TCI Chemicals related carbohydrate derivatives
• CymitQuimica acetyl azido galactopyranoses
• Glentham acetylated azido sugar catalog
• BOC Sciences azido sugar intermediate