4-Methylphenyl 2-O-benzoyl-3,6-O-dibenzyl-thio-β-D-glucopyranoside

4-Methylphenyl 2-O-benzoyl-3,6-O-dibenzyl-thio-β-D-glucopyranoside

CAS Number: Not Available
Catalog Number: A23-1023

Product Description:
4-Methylphenyl 2-O-benzoyl-3,6-O-dibenzyl-thio-β-D-glucopyranoside is a selectively protected thioglycoside derivative of D-glucose, 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 presence of benzoyl and benzyl protecting groups enables precise regioselective transformations. The benzoyl group at the 2-position can participate in neighboring group effects, assisting in stereoselective glycosylation, while the benzyl groups at the 3 and 6 positions offer stable protection and can be removed under hydrogenolysis conditions.

With its defined β-configuration and well-designed protecting group pattern, this compound is particularly valuable for the synthesis of complex oligosaccharides, glycoconjugates, and biologically active molecules. It is widely applied in medicinal chemistry, glycochemistry, and pharmaceutical intermediate development.

Key Features:

• Thioglycoside with 4-methylphenyl (p-tolyl) group
• Benzoyl protection at C-2 for stereochemical control
• Dibenzyl protection at C-3 and C-6
• Defined β-D-glucopyranoside configuration
• Efficient glycosyl donor for glycosylation reactions

Applications:

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

Molecular Formula: C₃₄H₃₄O₇S
Molecular Weight: 586.70 g/mol