4-Methylphenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

4-Methylphenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

CAS Number: 903906-55-8
Catalog Number: A23-1017

Product Description:
4-Methylphenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside is a selectively protected thioglycoside derivative of L-rhamnose, widely used as an advanced intermediate in carbohydrate chemistry and glycosylation reactions. The 4-methylphenyl (p-tolyl) thio group at the anomeric position provides excellent stability and serves as an efficient glycosyl donor upon activation.

The 2,3-O-isopropylidene (acetonide) protecting group enables regioselective transformations by protecting the vicinal diol, allowing targeted functionalization at other positions of the sugar ring. The defined α-configuration ensures stereochemical control in synthetic applications.

This compound is particularly valuable in the synthesis of oligosaccharides, glycoconjugates, and biologically active molecules. It is widely used in medicinal chemistry, glycochemistry, and pharmaceutical intermediate development due to its stability and controlled reactivity.

Key Features:

• Thioglycoside with 4-methylphenyl (p-tolyl) group
• 2,3-O-isopropylidene protection for regioselectivity
• Defined α-L-rhamnopyranoside configuration
• Effective glycosyl donor in glycosylation reactions
• High purity and reproducibility

Applications:

• Glycosylation and oligosaccharide synthesis
• Carbohydrate and glycochemistry research
• Glycoconjugate preparation
• Pharmaceutical intermediate development
• Selective protection and functionalization strategies

Molecular Formula: C₁₆H₂₂O₅S
Molecular Weight: 326.41 g/mol