Ethyl 4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

Ethyl 4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

Product Details

• CAS Number: 733002-14-7
• Catalog Number: A23-1050
• Molecular Formula: C25H30O5S
• Molecular Weight: 442.57 g/mol
• Purity: ≥ 98%

Description

Ethyl 4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside is a selectively protected thiomannoside designed for advanced carbohydrate synthesis. The benzylidene group at the 4,6-positions enables regioselective transformations, allowing controlled modification of other hydroxyl groups during multi-step synthesis.

The 3-O-(2-naphthalenylmethyl) substituent serves as a hydrophobic and selectively removable protecting group, providing flexibility in synthetic strategies. The thioglycoside functionality at the anomeric position offers stability and controlled activation, making this compound an effective glycosyl donor in the synthesis of mannose-containing oligosaccharides and glycoconjugates.

This compound is widely used in glycosylation reactions, oligosaccharide synthesis, and medicinal chemistry research.

Applications

• Glycosyl donor in carbohydrate synthesis
• Intermediate for regioselective protection strategies
• Building block for mannose-containing oligosaccharides
• Used in pharmaceutical and chemical research