8-Azidooctyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

8-Azidooctyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Basic Information

• Catalog Number: A23-1058
• Molecular Formula: C₂₂H₃₇N₃O₉
• Molecular Weight: 487.55 g/mol
• Purity: Typically ≥95% (HPLC/NMR)

Detailed Description

8-Azidooctyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside is a functionalized glucopyranoside derivative widely used in carbohydrate chemistry and bioconjugation applications. The molecule consists of a fully acetylated glucose unit linked to an 8 azidooctyl chain at the anomeric position, providing both structural protection and reactive functionality

The acetyl groups at positions 2, 3, 4, and 6 protect the hydroxyl functionalities of the sugar moiety, enhancing solubility in organic solvents and enabling controlled synthetic transformations. These protecting groups are commonly used in carbohydrate chemistry to facilitate selective reactions and stepwise synthesis

A key feature of this compound is the terminal azide group on the octyl chain, which serves as a highly versatile functional handle for click chemistry reactions, particularly copper catalyzed azide alkyne cycloaddition. This makes the compound especially valuable for the preparation of glycoconjugates, labeled biomolecules, and functional materials

The combination of a hydrophilic sugar moiety and a hydrophobic alkyl chain provides amphiphilic properties, making it suitable for applications involving membrane systems, nanomaterials, and surface functionalization

This compound is widely used in
Click chemistry and bioorthogonal reactions
Glycoconjugate and glycolipid synthesis
Surface modification and biomaterials research
Drug delivery and chemical biology
Advanced glycochemistry applications

The compound is typically obtained as a white to off white solid and ensures high reproducibility in multi step synthetic workflows

Key Features

Fully acetyl protected glucopyranoside
Contains azido functional group for click chemistry
Suitable for bioconjugation and labeling
Amphiphilic structure for advanced applications
High purity and synthetic reliability

Applications

Used in click chemistry and bioorthogonal reactions
Suitable for glycoconjugate and glycolipid synthesis
Applied in biomaterials and surface chemistry
Useful in pharmaceutical and chemical biology research

Storage and Handling

Store at 0 to minus 20 degree Celsius
Keep in a dry and moisture free environment
Protect from light and air exposure