1-S-tolyl-2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside

1-S-tolyl-2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside

CAS Number: Not Available
Catalog Number: A23-1013

Product Description:
1-S-tolyl-2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside is a highly functionalized and selectively protected glucose derivative used as an advanced intermediate in carbohydrate chemistry and organic synthesis. This compound features acetyl protecting groups at the 2, 3, and 4 positions, a tert-butyldimethylsilyl (TBDMS) group at the primary 6-position, and an S-tolyl group at the anomeric center, providing enhanced reactivity and versatility.

The combination of these protecting groups allows for precise regioselective transformations and controlled deprotection strategies during multi-step synthesis. The thioglycoside functionality (S-tolyl) makes it particularly useful as a glycosyl donor in glycosylation reactions, enabling the synthesis of complex oligosaccharides and glycoconjugates.

Due to its defined α-configuration and stable protected framework, this compound is widely applied in medicinal chemistry, glycochemistry, and pharmaceutical intermediate development.

Key Features:

• Tri-O-acetyl protection at positions 2, 3, and 4
• TBDMS-protected primary hydroxyl group (C-6)
• S-tolyl thioglycoside functionality (glycosyl donor)
• Defined α-D-glucopyranoside configuration
• Suitable for regioselective synthesis and glycosylation

Applications:

• Glycosylation and oligosaccharide synthesis
• Carbohydrate and glycochemistry research
• Glycoconjugate and nucleoside preparation
• Pharmaceutical intermediate development
• Advanced organic synthesis

Molecular Formula: C₂₈H₄₀O₉SSi
Molecular Weight: 580.76 g/mol