Ethyl 3-O-benzyl-1-thio-beta-D-glucopyranoside

Ethyl 3-O-benzyl-1-thio-β-D-glucopyranoside

Ethyl 3-O-benzyl-1-thio-β-D-glucopyranoside is a thioglycoside derivative used in synthetic carbohydrate chemistry, particularly for its role as a glycosyl donor in glycosylation reactions. Its structural features, including selective protection and the thioether linkage, make it a valuable intermediate for constructing oligosaccharides and glycoconjugates.

Chemical Identity

• Molecular Formula: C₁₅H₂₂O₄S
• Molecular Weight: ~314.40 g/mol
• Key Functional Groups:
  • Thioether linkage at the anomeric position for stability and controlled activation.
  • Benzyl group at the C-3 hydroxyl position for selective protection.
  • Ethyl group attached to the sulfur atom for hydrophobicity and reactivity.

Structural Features

1. Thioether Linkage at Anomeric Position:
   • The sulfur atom replaces the oxygen in glycosides, forming a thioglycoside. This substitution enhances stability during reactions and allows selective activation under mild conditions using promoters like NIS/TfOH.
2. 3-O-Benzyl Protection:
   • The benzyl group protects the hydroxyl group at C-3, preserving the integrity of the molecule during multi-step synthesis while allowing selective deprotection when needed.
3. β-Anomeric Configuration:
   • The β-configuration ensures specific stereochemical outcomes during glycosylation reactions, making it suitable for synthesizing β-linked oligosaccharides.

Applications

This compound is widely used in carbohydrate synthesis due to its tailored reactivity and protective groups:

• Glycosylation Reactions: Acts as a glycosyl donor in stereoselective synthesis of oligosaccharides and glycoconjugates. The thioether linkage allows precise activation, enabling controlled formation of glycosidic bonds.
• Intermediate for Complex Molecules: Used in the synthesis of biologically active natural products, glycolipids, and glycoproteins.
• Protective Group Manipulation: The benzyl group can be selectively removed under hydrogenolytic conditions to expose the hydroxyl group for further functionalization.

Reactivity Profile

The compound’s reactivity is influenced by its protective groups:

• The benzyl-protected hydroxyl ensures stability during reactions but can be selectively deprotected when required.
• The thioether linkage provides enhanced stability compared to standard glycosides but remains reactive under specific activation conditions.

Physical Properties

• Appearance: Typically a crystalline solid or powder.
• Solubility: Soluble in common organic solvents such as dichloromethane or chloroform due to its hydrophobic protective groups.

This compound exemplifies advanced design in carbohydrate chemistry, offering tailored reactivity for constructing complex oligosaccharides and glycoconjugates with applications in medicinal chemistry and materials science.

Citations:

1. https://pubchem.ncbi.nlm.nih.gov/compound/10094789