Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl azide

Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl azide is a specifically modified sugar derivative where the hydroxyl groups at the 2nd, 3rd, and 4th positions of the D-glucopyranuronic acid ring are acetylated, and the anomeric position is functionalized with an azido group (-N3). This compound is a white to pale brown crystalline solid widely used in synthetic carbohydrate chemistry, especially for bioorthogonal click chemistry applications. The presence of the azide group allows for highly selective conjugation reactions, making it critical for fluorescent labeling, drug conjugation, and biochemical probe development. Its chemical structure mimics D-glucuronic acid but has the added capacity for bio-conjugation, which aids in studies of glycan-protein interactions and enzymatic processes. The compound is delivered with high purity, backed by stringent quality control, and is stored under refrigerated conditions to maintain integrity for research, pharmaceutical, and diagnostic use.​

IUPAC Name

• Methyl (2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-azidooxane-2-carboxylate​

Appearance

• White to pale brown crystalline solid​

Source

• Chemically synthesized via selective acetylation and azido substitution of D-glucuronic acid derivatives​

Molecular Weight and Structure

• Molecular Formula: C13H19N3O9
• Molecular Weight: 361.30 g/mol​
• Structure: Acetylated glucopyranuronic acid ring with azido substitution and methyl ester at the anomeric carbon​
• SMILES: CO[C@H]1C@@HC@@HC@HC@HC1=O​

Sugar Specificity

• Modified D-glucuronic acid derivative with azido substitution
• Utilized in glycoscience and chemical biology as a functionalized sugar acid intermediate​

Biological Activity

• Enables bioorthogonal conjugation via azido group for labeling glycans, glycoproteins, and drugs
• Important in drug-delivery strategies, diagnostics, and molecular imaging
• Facilitates probing of glycan-protein interactions and glycosyltransferase activity​

Purity and Microbial Contamination

• Purity: ≥98% confirmed by spectral and chromatographic methods
• Chemical-grade with negligible microbial contamination ensured by synthesis and purification processes​

Identity and Quality Control

• Certified by NMR spectroscopy, mass spectrometry, and HPLC purity profiling
• Provided with Certificates of Analysis and safety data sheets (SDS)
• Melting point approx. 153 °C​

Shelf Life and Storage

• Store refrigerated at 2–8 °C
• Protect from light, moisture, and heat
• Shelf life up to 2 years under proper conditions​

Application

• Intermediate for the synthesis of azido-functionalized glycoconjugates
• Widely used in bioorthogonal click chemistry for molecular conjugation
• Supports research in glycomimetic drug development and glycan labeling
• Used in enzymatic and glycosylation studies for structural biology​

Key Characteristics

• Triacetylated methyl ester of 2-azido-2-deoxy-β-D-glucopyranuronic acid
• CAS number 67776-38-9
• Molecular weight 361.30 g/mol, white to pale brown crystalline solid
• High purity (>98%) and comprehensive analytical data
• Stable under refrigerated conditions
• Essential bioorthogonal reagent for glycobiology and chemical biology
• Enables targeted glycan conjugation and drug design
• Full identity confirmation with certificates and spectral data
• Supports synthetic, biochemical, and pharmacological research

Citations

• ChemicalBook product data​
• Apollo Scientific catalogue​
• PubChem glucopyranosyl azides​
• ChemSrc safety and identity​
• Glyco MindSynth glucopyranosyl azide​
• Sigma-Aldrich related acetyl sugars​
• SciDirect synthesis studies​
• ACS Publications glycomimetic synthesis​
• ChemImpex catalog​
• Glycomind Synth product range