3,7,8,9-Tetra-O-acetyl-6,6-dichloro-azabicyclo[12.2.2]sialyl phenylthioglycoside

3,7,8,9-Tetra-O-acetyl-6,6-dichloro-azabicyclo[12.2.2]sialyl phenylthioglycoside

3,7,8,9-Tetra-O-acetyl-6,6-dichloro-azabicyclo[12.2.2]sialyl phenylthioglycoside is a complex glycoside that incorporates a bicyclic structure with multiple acetyl groups and a phenylthiol moiety. This compound is of interest in organic synthesis and potential biological applications due to its unique structural features.

Structural Features

• Bicyclic Framework: The azabicyclo[12.2.2] structure consists of a nitrogen atom integrated into a bicyclic system, which contributes to the compound’s unique properties and reactivity.
• Acetyl Groups: The presence of four acetyl groups (tetra-O-acetyl) at positions 3, 7, 8, and 9 enhances the stability of the hydroxyl functionalities, allowing for selective reactions during synthetic processes.
• Dichloro Substitution: The 6,6-dichloro substitution introduces electron-withdrawing characteristics that can influence the compound’s reactivity and interactions with biological targets.
• Phenylthioglycoside Moiety: This component provides additional functionalization, enhancing solubility and reactivity. The thiol group can participate in nucleophilic reactions, making it useful in various synthetic applications.

Key Properties

• Molecular Formula: C₁₉H₂₃Cl₂N₁O₈S
• Molecular Weight: Approximately 482.36 g/mol
• Physical State: Typically appears as a white to off-white solid or crystalline powder.
• Solubility: Soluble in common organic solvents such as methanol and dichloromethane, 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 acetyl groups can be selectively removed to reveal functional hydroxyl groups for further reactions.
• Biochemical Research: It is valuable in studying carbohydrate-protein interactions and enzyme mechanisms due to its structural similarity to natural sialic acid derivatives.
• Pharmaceutical Development: The compound’s unique structure may be explored for potential therapeutic applications, particularly in drug design targeting glycan-related pathways and interactions.

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://pmc.ncbi.nlm.nih.gov/articles/PMC7561591/
2. https://pmc.ncbi.nlm.nih.gov/articles/PMC6273912/
3. https://pmc.ncbi.nlm.nih.gov/articles/PMC9781914/
4. https://pmc.ncbi.nlm.nih.gov/articles/PMC8708670/
5. https://patents.google.com/patent/US7868017B2/en
6. https://pmc.ncbi.nlm.nih.gov/articles/PMC7145827/
7. https://patents.google.com/patent/US5817679A/en
8. https://patents.google.com/patent/EP0272455B1/en