4-Methylphenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

4-Methylphenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

• CAS Number: 755002-33-6
• Catalog Number: A23-1053
• Molecular Formula: C₂₀H₂₂O₅S
• Molecular Weight: 374.45 g/mol
• Purity: Typically ≥95%

Detailed Description

4-Methylphenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside is a structurally refined thioglycoside derivative of D-mannose, widely used in advanced carbohydrate synthesis. The compound features a 4-methylphenyl (p-tolyl) thio group at the anomeric position, offering excellent stability and controlled activation during glycosylation reactions.

A key structural element of this molecule is the 4,6-O-benzylidene protecting group, which selectively locks the 4- and 6-hydroxyl groups of the mannose ring. This cyclic acetal protection plays a crucial role in directing regioselective glycosylation and enables selective functionalization at other hydroxyl positions, making it highly valuable for stepwise oligosaccharide assembly.

As a thioglycoside, this compound can be activated under mild conditions using promoters such as NIS/TfOH or other Lewis acids, facilitating efficient formation of glycosidic bonds with good stereocontrol. It is particularly useful in constructing α-mannosidic linkages, which are important in biologically active glycans.

The benzylidene group also contributes to conformational control and can be selectively opened to yield differentiated hydroxyl functionalities, enhancing its utility in complex carbohydrate synthesis.

This compound is widely used in:

• Oligosaccharide and polysaccharide synthesis
• Selective protection–deprotection strategies
• Glycoconjugate and glycoprotein research
• Development of carbohydrate-based therapeutics and vaccines
• Advanced glycochemistry and medicinal chemistry studies

It is typically supplied as a white to off-white crystalline solid, ensuring high reproducibility in sensitive synthetic applications.

Key Features

• High-purity benzylidene-protected thiomannoside
• Enables regioselective glycosylation strategies
• Stable thioglycoside glycosyl donor
• Contains 4,6-O-benzylidene protecting group
• Ideal for stepwise carbohydrate synthesis

Applications

• Glycosyl donor in oligosaccharide synthesis
• Used in selective protection and functionalization of sugars
• Important intermediate in glycoconjugate synthesis
• Applied in glycobiology and drug discovery research

 Storage & Handling

• Store at 0 to –20°C for long-term stability
• Keep in a dry, moisture-free environment
• Protect from light and air exposure