4-Methylphenyl 2-O-benzoyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside

4-Methylphenyl 2-O-benzoyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside

4-Methylphenyl 2-O-benzoyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside is a complex carbohydrate derivative commonly used in synthetic organic chemistry, particularly in the preparation of glycosides and oligosaccharides. This compound features multiple protective groups and a thioglycoside moiety, which enhances its utility as a glycosyl donor in stereoselective glycosylation reactions.

Chemical Identity

• Molecular Formula: C₃₂H₃₂O₆S
• Molecular Weight: Approximately 544.66 g/mol
• Functional Groups: Includes benzoyl, benzyl, and thioether functionalities.

Structural Features

1. Thioether Group at the Anomeric Position:
   • The sulfur atom at the anomeric center replaces the typical oxygen in glycosides, forming a thioglycoside. This substitution increases stability and allows for controlled activation during glycosylation reactions.
2. Protective Groups:
   • 2-O-Benzoyl Group: Protects the hydroxyl group at the C-2 position, preventing unwanted side reactions during synthesis.
   • 3,6-di-O-Benzyl Groups: Protect the hydroxyl groups at the C-3 and C-6 positions, offering stability while maintaining reactivity at other positions.
3. 4-Methylphenyl Aglycone:
   • The aglycone (non-sugar) portion is a 4-methylphenyl group attached to the anomeric sulfur atom, contributing to the compound’s hydrophobicity and reactivity in organic solvents.

Applications

This compound is particularly valuable in carbohydrate chemistry due to its well-defined protection pattern and thioglycoside functionality:

• Glycosylation Reactions: Acts as a glycosyl donor in stereoselective synthesis of oligosaccharides and glycoconjugates under mild activation conditions (e.g., using promoters like NIS/TfOH).
• Intermediate for Complex Molecules: Used in the synthesis of biologically active natural products, glycolipids, and glycoproteins.
• Selective Deprotection: The benzoyl and benzyl protecting groups can be selectively removed under specific conditions to expose hydroxyl groups for further derivatization.

Physical Properties (General Estimates Based on Similar Compounds)

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

Reactivity and Functionalization

The combination of protective groups and the thioether linkage allows for precise control over reactivity during multistep synthesis. For example:

• The benzoyl group can be removed via mild basic hydrolysis.
• Benzyl groups are typically cleaved using hydrogenolysis (e.g., Pd/C with hydrogen).

This compound serves as an excellent building block for constructing complex carbohydrate architectures with applications in medicinal chemistry and materials science.

Citations:

1. https://www.chemsrc.com/en/cas/20274-94-6_91115.html