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

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

CAS Number: 1828897-52-4
Catalog Number: A23-1024

Product Description:
4-Methylphenyl 2-O-benzoyl-3,6-O-dibenzyl-4-O-fluorenylcarboxymethyl-thio-β-D-glucopyranoside is a highly functionalized thioglycoside derivative of D-glucose designed for advanced carbohydrate synthesis and glycosylation strategies. The 4-methylphenyl (p-tolyl) thio group at the anomeric position provides excellent stability and serves as an efficient glycosyl donor upon activation.

This compound incorporates a benzoyl group at the 2-position for neighboring group participation, enabling stereoselective glycosylation. The benzyl groups at the 3 and 6 positions offer robust protection, while the fluorenylcarboxymethyl (Fmoc-like) functionality at the 4-position introduces orthogonal protection, allowing selective deprotection and further derivatization.

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

Key Features:

• Thioglycoside with 4-methylphenyl (p-tolyl) group
• Benzoyl group at C-2 for stereochemical control
• Dibenzyl protection at C-3 and C-6
• Fluorenylcarboxymethyl (Fmoc-like) protection at C-4
• Defined β-D-glucopyranoside configuration

Applications:

• Stereoselective glycosylation and oligosaccharide synthesis
• Carbohydrate and glycochemistry research
• Glycoconjugate preparation
• Pharmaceutical intermediate development
• Orthogonal protection and multi-step synthesis strategies

Molecular Formula: C₄₈H₄₄O₉S
Molecular Weight: 796.92 g/mol