3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

Basic Information

• CAS Number: 2765598-92-1
• Catalog Number: A23-1056
• Molecular Formula: C₁₈H₁₉NO₉
• Molecular Weight: 393.35 g/mol
• Purity: Typically ≥95% (HPLC/NMR)

Detailed Description

3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose is a highly functionalized glucopyranose derivative widely used in carbohydrate chemistry as an important intermediate for the synthesis of amino sugars and glycoconjugates. The molecule contains acetyl protecting groups at the 3, 4, and 6 positions, which enhance solubility and stability while enabling controlled synthetic transformations

A defining feature of this compound is the phthalimido group at the C2 position, which serves as a protected amine functionality. This group is particularly valuable in synthetic chemistry because it can be converted into a free amino group under controlled conditions, making it a key precursor for the preparation of 2-amino-2-deoxy sugars

The acetyl groups provide temporary protection of hydroxyl functionalities, allowing selective reactions at other positions. This makes the compound highly suitable for stepwise synthesis and modification of complex carbohydrate structures

Due to its well designed protection pattern, this compound is widely used in
Oligosaccharide synthesis
Glycosaminoglycan and amino sugar preparation
Glycoconjugate and glycoprotein research
Carbohydrate based drug and vaccine development
Advanced glycochemistry and medicinal chemistry studies

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

Key Features

Acetyl protected glucopyranose derivative
Contains phthalimido protected amino functionality
Suitable for amino sugar synthesis
Stable intermediate for multi step reactions
High purity and reproducibility

Applications

Used in oligosaccharide synthesis
Precursor for amino sugar derivatives
Applied in glycoconjugate and glycoprotein research
Useful in pharmaceutical and carbohydrate chemistry

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