4-Methylphenyl 2-O-benzyl-3,4-di-O-benzoyl-1-thio-β-L-fucopyranoside

4-Methylphenyl 2-O-benzyl-3,4-di-O-benzoyl-1-thio-β-L-fucopyranoside

4-Methylphenyl 2-O-benzyl-3,4-di-O-benzoyl-1-thio-β-L-fucopyranoside is a specialized glycoside derivative that incorporates a fucopyranoside structure modified with multiple benzoyl and benzyl groups. This compound is significant in organic synthesis and biochemical research due to its unique features.

Structural Features

• Core Structure: The compound is based on a β-L-fucopyranoside framework, which consists of a six-membered ring containing five carbon atoms and one oxygen atom, characteristic of sugar derivatives.
• Substituents:
  • 4-Methylphenyl Group: This aromatic substituent enhances the lipophilicity of the molecule and may influence its biological interactions.
  • 2-O-Benzyl Group: Provides additional steric bulk and stability to the compound while enhancing solubility in organic solvents.
  • 3,4-Di-O-benzoyl Groups: These two benzoyl groups at positions 3 and 4 serve as protecting groups for the hydroxyl functionalities, increasing the compound’s stability and allowing for selective reactions during synthesis.
  • Thioether Linkage: The presence of a thio group (-S-) in place of one of the hydroxyl groups introduces unique reactivity patterns, particularly in nucleophilic substitution reactions.

Key Properties

• Molecular Formula: C₁₉H₁₉N₁O₅S
• Molecular Weight: Approximately 389.43 g/mol
• Physical State: Typically appears as a white to off-white solid or crystalline powder.
• Solubility: Soluble in common organic solvents such as dichloromethane and methanol, facilitating its use in various synthetic applications.

Applications

• Organic Synthesis: This compound serves as an important intermediate in the synthesis of more complex carbohydrates and glycosides. The benzoyl groups can be selectively removed to reveal functional hydroxyl groups for further reactions.
• Biochemical Research: It is valuable in studying carbohydrate-protein interactions, enzyme mechanisms, and glycosylation processes due to its structural similarity to natural fucose-containing molecules.
• Pharmaceutical Development: The compound’s unique structure may be explored for potential therapeutic applications, particularly in drug design targeting glycan-related pathways.

Safety and Handling

While specific safety data for this compound may not be extensively documented, standard laboratory precautions should be taken when handling organic chemicals. Proper personal protective equipment (PPE) such as gloves and goggles is recommended to minimize exposure.

This compound exemplifies the integration of carbohydrate chemistry with synthetic organic methods, offering valuable insights and tools for researchers in both academic and industrial settings.

Citations:

1. https://www.chemsrc.com/en/cas/24332-98-7_684579.html
2. https://pubchem.ncbi.nlm.nih.gov/compound/Methyl-alpha-L-fucopyranoside
3. https://pubchem.ncbi.nlm.nih.gov/compound/Methyl-alpha-D-fucopyranoside
4. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3184961.htm
5. https://www.chemimpex.com/products/32198
6. https://www.chemicalbook.com/ProductChemicalPropertiesCB3184961_EN.htm
7. https://www.tcichemicals.com/IN/en/p/M1051
8. https://www.sigmaaldrich.com/IN/en/product/sigma/m8527