p-Tolyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

p-Tolyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

CAS Number: 942043-30-3
Catalog Number: A23-1025

Product Description:
p-Tolyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside is a selectively protected thioglycoside derivative of D-glucose, widely utilized as an advanced intermediate in carbohydrate chemistry and glycosylation reactions. The p-tolyl thio group at the anomeric position provides excellent stability and serves as an efficient glycosyl donor upon activation.

The benzoyl group at the 2-position enables neighboring group participation, promoting stereoselective glycosylation. The benzyl group at the 3-position offers stable protection, while the 4,6-O-benzylidene acetal provides regioselective protection of the diol, facilitating targeted functionalization at other positions of the sugar ring.

With its well-defined β-configuration and strategically 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 glycochemistry, medicinal chemistry, and pharmaceutical intermediate development.

Key Features:

• p-Tolyl thioglycoside functionality (glycosyl donor)
• Benzoyl group at C-2 for stereochemical control
• Benzyl protection at C-3
• 4,6-O-benzylidene protection for regioselectivity
• Defined β-D-glucopyranoside configuration

Applications:

• Stereoselective glycosylation and oligosaccharide synthesis
• Carbohydrate and glycochemistry research
• Glycoconjugate preparation
• Pharmaceutical intermediate development
• Advanced protection and deprotection strategies

Molecular Formula: C₃₄H₃₂O₈S
Molecular Weight: 600.68 g/mol