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

3,4,6-Tri-O-acetyl-2-azido-2-deoxy-D-galactopyranose is a synthetic carbohydrate derivative featuring acetylation at the 3rd, 4th, and 6th hydroxyl groups of D-galactopyranose, combined with the substitution of the hydroxyl group at carbon-2 by an azido (-N3) functional group. This compound appears as a white crystalline solid and is extensively used in advanced carbohydrate chemistry, particularly in the synthesis of azido sugars essential for bioorthogonal click chemistry reactions. Its azido group enables highly selective conjugation reactions that allow for the tagging and modification of biomolecules such as glycoconjugates, enabling targeted drug delivery and diagnostic applications. Chemically stable and pure, it serves as a versatile intermediate in the design of glycomimetics and glycoconjugates that are pivotal in studying carbohydrate-protein interactions, enzymatic glycosylation, and the development of novel therapeutics. It is supplied with guaranteed high purity and supported by comprehensive identity and quality control data.

IUPAC Name

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

Appearance

• White crystalline powder

Source

• Chemically synthesized from D-galactose derivatives by selective acetylation and azido substitution at position 2

Molecular Weight and Structure

• Molecular Formula: C12H17N3O8
• Molecular Weight: 335.28 g/mol
• Structure: D-galactopyranose ring acetylated at positions 3,4,6 with azido substitution at C2
• SMILES: CC(=O)O[C@H]1OC(OC(C)=O)C@HC@@H[C@H]1OC(C)=O

Sugar Specificity

• Azido-substituted D-galactose derivative with multiple acetyl groups increasing lipophilicity and stability
• Utilized for selective glycosylation and conjugation reactions in carbohydrate synthesis

Biological Activity

• Serves as precursor in bioorthogonal click chemistry for conjugation and labeling of glycans and biomolecules
• Supports drug discovery by enabling selective attachment of sugars to proteins and drugs
• Facilitates investigation of carbohydrate-binding proteins and glycosyltransferase enzymes

Purity and Microbial Contamination

• Maintained at ≥98% purity confirmed by NMR and chromatographic methods
• Chemically pure with no significant microbial contamination due to manufacturing standards

Identity and Quality Control

• Identity ensured by nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and HPLC
• Melting point reported approximately 83-87 °C
• Certificate of Analysis and SDS typically provided

Shelf Life and Storage

• Recommended storage at 0 to -20 °C in sealed, dry containers
• Protect from light and moisture
• Shelf life can extend to 2 years under these conditions

Application

• Intermediate for synthesis of azido glycans in medicinal and synthetic carbohydrate chemistry
• Used in click chemistry for cell labeling, drug conjugation, and diagnostics
• Enables development of glycomimetics and targeted therapeutic agents
• Facilitates biochemical research on glycan structure and function
• Supports enzyme assay studies and glycosylation mechanism exploration

Key Characteristics

• Tri-O-acetylated 2-azido-2-deoxy-D-galactopyranose derivative
• CAS number 188226-30-9
• Molecular weight 335.28 g/mol, white crystalline solid
• High purity (>98%) and well-characterized
• Stable under refrigerated storage
• Versatile precursor for bioorthogonal chemical tagging
• Enables advanced glycoconjugate and glycomimetic synthesis
• Rigorous quality control with comprehensive documentation
• Essential for click chemistry and carbohydrate-related drug development
• Supports research in glycobiology and diagnostic development

Citations

• Synthose 3,4,6-Tri-O-acetyl-2-azido-2-deoxy-D-galactopyranose
• ChemicalBook azido sugar derivative
• CymitQuimica product info
• PubChem galactopyranose derivatives
• MedChemExpress azido sugar standards
• Google Patents synthetic methodologies
• TCI Chemicals carbohydrate derivatives
• Sigma-Aldrich acetylated sugars
• BOC Sciences carbohydrate intermediates
• Glentham azido sugar catalog