p-Tolyl 1-thio-α-D-mannopyranoside

p-Tolyl 1-thio-α-D-mannopyranoside

 Basic Information

• CAS Number: 457931-46-3
• Catalog Number: A23-1052
• Molecular Formula: C₁₃H₁₈O₅S
• Molecular Weight: 286.34 g/mol

 Detailed Description

p-Tolyl 1-thio-α-D-mannopyranoside is a versatile thioglycoside derivative of D-mannose, widely used in carbohydrate chemistry as a stable and efficient synthetic intermediate. The molecule features a p-tolyl thio group at the anomeric position, which enhances stability while allowing controlled activation during glycosylation reactions.

Thioglycosides are particularly valuable in glycochemistry due to their ability to act as latent glycosyl donors, which can be selectively activated under mild conditions using promoters such as NIS/TfOH or other Lewis acids. This property enables precise formation of glycosidic bonds, making this compound suitable for the synthesis of structurally complex carbohydrates.

The α-anomeric configuration of this mannopyranoside is especially important for constructing biologically relevant glycans, including α-mannosidic linkages, which are commonly found in glycoproteins and other natural products. Its unprotected hydroxyl groups also provide flexibility for further functionalization, protection, or derivatization depending on synthetic requirements.

Due to its stability, reactivity, and structural reliability, this compound serves as a key intermediate in:

• Oligosaccharide and polysaccharide synthesis
• Glycoconjugate and glycoprotein research
• Development of carbohydrate-based therapeutics and vaccines
• Advanced studies in glycobiology and medicinal chemistry

The compound is typically obtained as a white to off-white solid, ensuring consistent performance in sensitive synthetic workflows.

Key Features

• High-purity thiomannoside derivative
• Stable thioglycoside intermediate
• Contains p-tolyl thio functionality
• Suitable for glycosylation reactions
• Useful for carbohydrate synthesis and modification

 Applications

• Intermediate in carbohydrate and oligosaccharide synthesis
• Used in glycosyl donor preparation
• Applied in glycoconjugate and glycobiology research
• Supports medicinal chemistry and sugar-based drug development

 Storage & Handling

• Store in a cool, dry place
• Keep container tightly closed
• Protect from moisture and light