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

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

4-Methylphenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside is a specialized glycoside derivative that plays a significant role in organic synthesis and biochemical research. This compound features a fucopyranoside structure modified with multiple benzyl protecting groups, enhancing its stability and reactivity.

Structural Features

• Core Structure: The compound is based on the β-L-fucopyranoside framework, which consists of a six-membered ring containing five carbon atoms and one oxygen atom.
• Substituents:
  • 4-Methylphenyl Group: This aromatic substituent increases the lipophilicity of the molecule and can influence its biological interactions.
  • Tri-O-benzyl Groups: The three benzyl groups (attached at the 2, 3, and 4 positions) serve as protecting groups that stabilize the hydroxyl functionalities during synthetic processes. They also enhance the solubility of the compound in organic solvents.
  • Thioether Linkage: The presence of a thio group (-S-) in place of one of the hydroxyl groups allows for unique reactivity patterns, particularly in nucleophilic substitution reactions.

Key Properties

• Molecular Formula: C₃₄H₃₆O₄S
• Molecular Weight: Approximately 540.71 g/mol
• Physical State: Typically appears as a white to off-white solid or crystalline powder.
• Melting Point: Reported melting point ranges from approximately 53 to 58 °C, indicating moderate thermal stability.
• Solubility: Slightly soluble in common organic solvents such as chloroform and methanol, facilitating its use in various synthetic applications.

Applications

• Organic Synthesis: This compound is utilized as an intermediate in the synthesis of more complex carbohydrates and glycosides. The benzyl protecting groups can be selectively removed to reveal functional hydroxyl groups for further reactions.
• Biochemical Research: It serves as a valuable tool 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.tcichemicals.com/ID/en/p/M1628
2. https://www.sigmaaldrich.com/TR/en/product/apolloscientificltd/apoh99bfb8c3?context=bbe
3. https://synthose.com/products/MG239
4. https://www.bocsci.com/product/4-methylphenyl-2-3-4-tri-o-benzyl-1-thio-l-cas-211801-54-6-339116.html
5. https://www.glentham.com/en/products/product/GC7908/
6. https://synthose.com/products/MF601
7. https://ppbanalytical.com/product/4-methylphenyl-234-tri-o-benzyl-1-thio-%CE%B2-l-fucopyranoside/
8. https://www.biosynth.com/p/MM08172/177943-74-7-4-methylphenyl-234-tri-o-benzyl-b-d