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

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

CAS Number: 473711-83-0
Catalog Number: A23-1026

Product Description:
p-Tolyl 3-O-benzyl-4,6-O-benzylidene-1-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 p-tolyl thio group at the anomeric position provides excellent stability and serves as an efficient glycosyl donor upon activation.

The benzyl group at the 3-position offers stable protection, while the 4,6-O-benzylidene acetal provides regioselective protection of the diol, enabling controlled functionalization at other positions of the glucose ring. The defined β-configuration ensures stereochemical precision in glycosylation processes.

With its well-balanced protecting group strategy and reliable reactivity, this compound is particularly valuable for the synthesis of 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)
• Benzyl protection at C-3
• 4,6-O-benzylidene acetal for regioselectivity
• Defined β-D-glucopyranoside configuration
• Suitable for stereoselective glycosylation

Applications:

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

Molecular Formula: C₂₇H₂₈O₆S
Molecular Weight: 480.58 g/mol