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

1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose is a chemically synthesized sugar derivative used extensively in carbohydrate chemistry and glycobiology. It features acetylation at positions 1, 3, 4, and 6 of the glucopyranose ring, with the hydroxyl group at position 2 substituted by an azido (-N3) group. This compound serves as a crucial intermediate for the synthesis of azido sugars, which are indispensable in bio-orthogonal click chemistry for selective labeling, conjugation, and modification of glycans and other biomolecules. Due to its reactivity and structural specificity, it is exploited in drug design, glycomimetic synthesis, and biochemical studies investigating carbohydrate-protein interactions and enzymatic processes. The compound is a white crystalline powder with a high purity grade, and it is stored under controlled conditions to maintain stability and performance for therapeutic and research applications.

IUPAC Name

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

Appearance

• White crystalline solid

Source

• Synthesized by acetylation and azido-substitution on D-glucopyranose precursors

Molecular Weight and Structure

• Molecular Formula: C14H18N3O9
• Molecular Weight: 375.31 g/mol
• Structure: Acetylated D-glucopyranose ring with azido substituent at C-2; 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

• Derivative of D-glucose with azido substitution at C2 and acetylation at key hydroxyls
• Used as a versatile intermediate in glucoside and glycomimetic chemistry

Biological Activity

• Enables synthesis of azide-functionalized glycomolecules for bio-orthogonal labeling and conjugation
• Facilitates biochemical studies of glycan recognition and enzyme specificity
• Plays a role in research targeting carbohydrate-binding proteins for therapeutic development

Purity and Microbial Contamination

• Typically ≥98% purity confirmed by 1H-NMR and HPLC
• Chemical-grade, free from microbial contamination due to synthetic preparation and purification

Identity and Quality Control

• Characterized and verified by NMR, MS, and chromatographic profiling
• Supplied with Certificates of Analysis and Safety Data Sheets
• Melting point approximately 120–125 °C

Shelf Life and Storage

• Store at 0 to -20 °C in airtight containers
• Protect from moisture, heat, and light
• Shelf life extends to 2 years or more under proper storage

Application

• Key intermediate for click chemistry and azido sugar glycoconjugate synthesis
• Utilized in studies of carbohydrate-protein interactions and glycosyltransferase activity
• Supports drug discovery, diagnostics, and bio-conjugation techniques
• Enables preparation of novel glycomimetics and carbohydrate-based therapeutics

Key Characteristics

• 2-Azido-2-deoxy tetra-acetylated derivative of D-glucopyranose
• CAS number 1092318-60-8
• Molecular weight 375.31 g/mol, white crystalline solid
• High chemical purity (≥98%) certified for research use
• Stable under refrigerated storage conditions
• Critical reagent in synthetic and medicinal carbohydrate chemistry
• Facilitates bio-orthogonal labeling via click chemistry
• Full analytical characterization for identity and purity supplied
• Enables study of glycan function and synthesis of glycoconjugates

Citations

• MedChemExpress 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose
• Synthose azido sugar derivative
• ChemicalBook acetyl-azido glucopyranoses
• Sigma-Aldrich related sugars
• TCI Chemicals carbohydrate derivatives
• Google Patents synthesis methods
• Glentham catalog and usage
• CymitQuimica azido sugar catalog
• BOC Sciences glycoside intermediates
• PMC published glycoscience articles