4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside

4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside

• CAS Number: 211801-79-5
• Catalog Number: A23-1051
• Molecular Formula: C₂₁H₂₆O₉S
• Molecular Weight: 454.49 g/mol

4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside is a highly functionalized thioglycoside derivative of D-mannose, widely utilized as a reliable glycosyl donor in advanced carbohydrate synthesis. The molecule features a 4-methylphenyl (p-tolyl) thio group at the anomeric position, providing enhanced stability and controlled reactivity during glycosylation reactions.

The presence of acetyl protecting groups at the 2, 3, 4, and 6 positions improves solubility in organic solvents and prevents unwanted side reactions, enabling precise regioselective and stereoselective transformations. These protecting groups are particularly beneficial in stepwise oligosaccharide assembly and complex glycoconjugate synthesis.

As a thioglycoside, this compound can be activated under mild conditions using promoters such as NIS/TfOH or other Lewis acids, allowing efficient formation of glycosidic bonds with high stereocontrol. It is especially useful in constructing α-mannosidic linkages, which are often challenging in carbohydrate chemistry.

Due to its stability and versatility, it serves as an important intermediate in:

• Oligosaccharide and polysaccharide synthesis
• Glycoprotein and glycolipid research
• Vaccine and drug development involving carbohydrate antigens
• Structure–function studies in glycobiology

The compound is typically obtained as a white to off-white crystalline powder with high purity, ensuring reproducibility in sensitive synthetic workflows.

Key Features

• High-purity thioglycoside mannose derivative
• Typically ≥95–98% purity (HPLC / NMR)
• Stable acetyl-protected sugar intermediate
• Suitable for glycosylation reactions & carbohydrate synthesis
• Good solubility in organic solvents (DMSO, MeOH, DCM, etc.)

Applications

• Glycosyl donor in oligosaccharide synthesis
• Research in glycochemistry & glycobiology
• Intermediate for pharmaceutical and carbohydrate-based drug development
• Used in thioglycoside-based glycosylation strategies

Storage & Handling

• Storage Temperature: 0 to –20°C recommended
• Store in a cool, dry, moisture-free environment
• Handle under inert conditions for best stability