Benzyl-Protected Glucoside: A Building Block for Carbohydrate Synthesis (CAS 59935-49-8)

Benzyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside is a protected glucose derivative used in selective functionalization and the assembly of complex carbohydrates and glycoconjugates.

Chemical information

Chemical name: Benzyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside. Common name: Benzyl-protected glucoside. Molecular formula: C34H36O6. Molecular weight: 540.65 g/mol. CAS number: 59935-49-8. Classification: Important intermediates; glucose.

Structural features

Benzyl ethers mask the hydroxyl groups at C2, C3, and C4, reducing unwanted reactions and allowing later removal, for example by catalytic hydrogenation. A benzyl glycosidic group occupies the anomeric position, providing a stable starting point for further modification. The defined α-D-glucopyranoside configuration is useful in routes that require control of carbohydrate stereochemistry.

Applications

Complex carbohydrate synthesis

This intermediate can be elaborated into donor or acceptor building blocks for oligosaccharides, polysaccharides, and glycoconjugates. The benzyl groups can remain in place during assembly and be removed at a later stage. Possible applications include glycan probes, materials, and carbohydrate-based drug research.

Glycosylation

The anomeric benzyl group can serve as temporary protection. After suitable deprotection or activation, the anomeric position can be used to connect another sugar or ligand in routes to glycolipids, glycoprotein mimics, and carbohydrate-containing natural products.

Medicinal chemistry and bioconjugation

Further modification can introduce bioorthogonal groups for coupling to proteins, nucleic acids, or other carriers in targeted delivery and glycobiology research.

Synthetic methodology

The compound can serve as a model substrate for comparing protecting-group strategies, stereoselective glycosylation, and catalytic hydrogenation conditions.

Conclusion

Its defined configuration and removable protection make this glucoside a practical starting point for more complex carbohydrate structures.

Prepared by KASONS. For research use only.