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

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

Basic Information

• Catalog Number: A23-1057
• Molecular Formula: C₂₂H₃₇BrO₉
• Molecular Weight: 525.43 g/mol
• Purity: Typically ≥95% (HPLC/NMR)

Detailed Description

8-Bromooctyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside is a functionalized glucopyranoside derivative designed for advanced carbohydrate and glycoconjugate synthesis. The molecule consists of a fully acetylated glucose moiety linked to an 8 bromooctyl chain at the anomeric position, providing both protection and functional versatility

The acetyl groups at positions 2, 3, 4, and 6 serve as protective groups for the hydroxyl functionalities, enhancing solubility in organic solvents and enabling controlled chemical transformations. These protecting groups are commonly used in carbohydrate synthesis to prevent side reactions and to allow selective deprotection strategies

A key feature of this compound is the terminal bromine functional group on the octyl chain. This reactive site allows further chemical modification through nucleophilic substitution reactions, making it highly suitable for the synthesis of glycoconjugates, glycolipids, and surface functionalized biomolecules

The presence of the hydrophobic alkyl chain combined with the hydrophilic sugar moiety makes this compound particularly useful in studies involving amphiphilic systems and membrane associated glycans

This compound is widely used in
Glycoconjugate and glycolipid synthesis
Surface modification and linker chemistry
Drug delivery and biomaterials research
Carbohydrate based medicinal chemistry
Advanced glycochemistry applications

The compound is typically obtained as a white to off white solid and provides reliable performance in multi step synthetic workflows

Key Features

Fully acetyl protected glucopyranoside
Contains reactive bromooctyl linker
Suitable for conjugation and derivatization
Amphiphilic structure for biomaterial applications
High purity and synthetic reliability

Applications

Used in glycoconjugate and glycolipid synthesis
Suitable for linker and spacer introduction
Applied in biomaterials and surface chemistry
Useful in pharmaceutical and carbohydrate 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