4-Methylphenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

4-Methylphenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

4-Methylphenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside is a specialized thioglycoside derivative utilized in carbohydrate chemistry, particularly in the synthesis of oligosaccharides and glycoconjugates. This compound features an α-D-mannopyranoside core with protective groups that enhance its reactivity and facilitate selective transformations during glycosylation processes.

Structural Features

• Core Structure: The backbone consists of an α-D-mannopyranoside unit with a thio group at the anomeric position (C1), which enhances its reactivity as a glycosyl donor.
• Protective Groups:
  • Benzylidene group at O-4 and O-6, providing stable acetal protection that prevents unwanted reactions while allowing for selective transformations.
  • Benzyl group at O-3, which adds stability and facilitates controlled reactions without interfering with other functional groups.
  • 4-Methylphenyl group at the anomeric thio position, enhancing solubility and potentially influencing the reactivity of the glycosyl donor.

Synthesis Strategy

The synthesis typically involves several key steps:

1. Benzylidene Formation: The hydroxyl groups at O-4 and O-6 are protected by forming a benzylidene acetal using benzaldehyde derivatives under acidic conditions.
2. Benzyl Protection: The hydroxyl group at O-3 is protected using benzyl bromide in the presence of a suitable base to introduce the benzyl protecting group.
3. Thioether Formation: The thio group is introduced at the anomeric position through thiol substitution, enhancing the compound’s glycosyl donor properties.

Physicochemical Properties

• Molecular Formula: Estimated as C₃₄H₃₈O₇S based on the substituent analysis.
• Appearance: Typically appears as a white crystalline solid, common for similar compounds in carbohydrate chemistry.
• Solubility: Soluble in polar aprotic solvents such as DMSO, DMF, and dichloromethane (DCM).
• Storage Conditions: Recommended to be stored at low temperatures (−20°C) under inert atmosphere to maintain stability.

Applications

• This compound serves as an important intermediate in synthesizing glycoconjugates and oligosaccharides due to its orthogonal protecting groups that allow for selective deprotection and further functionalization.
• It can also be utilized in studies related to glycan biology, facilitating the exploration of glycan interactions and functions in various biological systems.

Safety and Handling

• Generally considered non-hazardous but standard laboratory precautions should be observed when handling organic compounds.
• Use gloves and work in a well-ventilated area or fume hood to minimize exposure.

This compound exemplifies advanced strategies in carbohydrate synthesis, showcasing how protective group chemistry can be leveraged to achieve complex glycosidic structures efficiently.

Citations:

1. https://www.beilstein-journals.org/bjoc/articles/21/27
2. https://pmc.ncbi.nlm.nih.gov/articles/PMC6259426/
3. https://application.wiley-vch.de/books/sample/3527340106_c01.pdf
4. https://pubs.acs.org/doi/10.1021/ed074p1297
5. https://pmc.ncbi.nlm.nih.gov/articles/PMC8423405/
6. https://pubs.rsc.org/en/content/articlelanding/2017/ob/c6ob02278b
7. https://pubs.acs.org/doi/10.1021/ol401166x