4-Methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-(9-fluorenylmethoxycarbonyl)-1-thio-beta-D-glucopyranoside

4-Methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-(9-fluorenylmethoxycarbonyl)-1-thio-beta-D-glucopyranoside

Basic Information

• Catalog Number: A23-1062
• Molecular Formula: C₄₈H₄₄O₉S
• Molecular Weight: 804.92 g/mol
• Purity: Typically ≥95% (HPLC/NMR)

Detailed Description

4-Methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-(9-fluorenylmethoxycarbonyl)-1-thio-beta-D-glucopyranoside is a highly advanced thioglycoside derivative designed for precision controlled carbohydrate synthesis. The molecule features a 4 methylphenyl thio group at the anomeric position which provides stability and allows selective activation during glycosylation reactions

The compound incorporates a strategically designed protecting group pattern to enable stereoselective and regioselective transformations. The benzoyl group at the C2 position plays a key role in neighboring group participation, facilitating controlled formation of glycosidic bonds. The benzyl groups at the C4 and C6 positions provide stability and can be selectively removed under hydrogenolysis conditions

A key highlight of this molecule is the presence of a 9 fluorenylmethoxycarbonyl group at the C3 position, which introduces an orthogonal protection strategy. This allows selective deprotection under mild basic conditions without disturbing other protecting groups, making the compound highly suitable for stepwise oligosaccharide synthesis

As a thioglycoside, the compound can be activated using standard promoters, enabling efficient glycosidic bond formation with high stereocontrol. The beta configuration of the glucopyranoside further supports its use in constructing biologically relevant glycans

This compound is widely used in
Complex oligosaccharide synthesis
Orthogonal protection strategies
Glycoconjugate and glycoprotein research
Carbohydrate based drug development
Advanced glycochemistry and medicinal chemistry

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

Key Features

Highly functionalized protected thioglucoside
Benzoyl group enables stereoselective glycosylation
Benzyl protections allow selective deprotection
Fmoc group provides orthogonal protection strategy
Suitable for complex carbohydrate synthesis

Applications

Used in advanced oligosaccharide synthesis
Suitable for glycoconjugate and glycoprotein research
Applied in pharmaceutical and carbohydrate chemistry
Useful in glycoengineering and medicinal 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