Methyl (phenyl 5-acetoamido-8-O-tert-butyldimethylsilyl-5-N,4-O-carbonyl-7-O,9-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate

Methyl (phenyl 5-acetoamido-8-O-tert-butyldimethylsilyl-5-N,4-O-carbonyl-7-O,9-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate

Methyl (phenyl 5-acetoamido-8-O-tert-butyldimethylsilyl-5-N,4-O-carbonyl-7-O,9-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate is a complex glycoside derivative that incorporates multiple functional groups, making it significant in organic synthesis and biochemical research. Below is a detailed description of its structure, properties, and applications.

Structural Features

• Core Structure: The compound is based on a nonulopyranoside framework, specifically derived from D-galacto sugars. It features a six-membered ring with five carbon atoms and one oxygen atom.
• Substituents:
  • 5-Acetamido Group: This group enhances the compound’s solubility and reactivity, providing a site for further chemical modifications.
  • 8-O-tert-butyldimethylsilyl (TBDMS) Group: This protecting group stabilizes the hydroxyl functionality at position 8, allowing for selective reactions without interfering with other functional groups.
  • 5-N,4-O-Carbonyl and 7-O,9-O-Carbonyl Groups: These carbonyl functionalities increase the reactivity of the molecule, facilitating various synthetic pathways.
  • 2-Thio Group: The presence of sulfur in the structure introduces unique reactivity patterns, particularly in nucleophilic substitution reactions.

Key Properties

• Molecular Formula: C₁₉H₃₁N₃O₇S
• Molecular Weight: Approximately 421.54 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 TBDMS group 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 sugar derivatives.
• 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://pubchem.ncbi.nlm.nih.gov/compound/5-O-DMT-2-O-TBDMS-N-Ac-cytidine
2. https://pubchem.ncbi.nlm.nih.gov/compound/Methyl-p-tert-butylphenylacetate
3. https://www.rsc.org/suppdata/d0/cc/d0cc05901c/d0cc05901c1.pdf
4. https://www.sigmaaldrich.com/IN/en/product/aldrich/190500
5. https://www.sciencedirect.com/science/article/abs/pii/S1385894713011820
6. https://www.glentham.com/en/products/categories/all/view-50-all/?q=&page=497
7. https://pubs.acs.org/doi/10.1021/jm00050a015
8. https://www.sciencedirect.com/topics/chemistry/tert-butyldimethylsilyl-group