p-Tolyl 2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside

p-Tolyl 2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside

 Basic Information

• CAS Number: 1407151-98-7
• Catalog Number: A23-1054
• Molecular Formula: C₃₄H₃₄O₆S
• Molecular Weight: 570.69 g/mol
• Purity: Typically ≥95% (HPLC/NMR)

Detailed Description

p-Tolyl 2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-mannopyranoside is a highly functionalized thioglycoside derivative of D-mannose, designed for precision-driven carbohydrate synthesis. The molecule incorporates a p-tolyl thio group at the anomeric position, providing stability and enabling controlled activation in glycosylation reactions.

This compound features a strategically designed protecting group pattern, including a benzoyl ester at the C-2 position and benzyl ether protections at the C-3 and C-4 positions. The benzoyl group plays a crucial role in neighboring group participation, which helps direct the stereochemical outcome of glycosylation reactions. Meanwhile, the benzyl groups provide stability and can be selectively removed under hydrogenolysis conditions, allowing further functionalization.

Such a protection strategy makes this molecule particularly valuable in constructing stereoselective glycosidic linkages, especially in the synthesis of complex oligosaccharides and glycoconjugates. The combination of protecting groups allows chemists to carefully control both reactivity and selectivity during multi-step synthesis.

As a thioglycoside, it can be activated using common promoters such as NIS/TfOH or other Lewis acids, enabling efficient glycosidic bond formation under mild conditions.

This compound is widely used in:

• Oligosaccharide and polysaccharide synthesis
• Stereoselective glycosylation strategies
• Glycoconjugate and glycoprotein research
• Carbohydrate-based drug and vaccine development
• Advanced glycochemistry and medicinal chemistry

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

Key Features

• Highly functionalized protected thiomannoside
• Benzoyl group enables neighboring group participation
• Benzyl protections allow selective deprotection
• Stable and efficient thioglycoside glycosyl donor
• Ideal for stereoselective carbohydrate synthesis

Applications

• Glycosyl donor in complex oligosaccharide synthesis
• Used in stereoselective glycosylation reactions
• Intermediate in glycoconjugate synthesis
• Applied in glycobiology and pharmaceutical 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