4-Methylphenyl 3,4,6-tri-O-benzyl-2-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-galactopyranoside

4-Methylphenyl 3,4,6-tri-O-benzyl-2-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-galactopyranoside

4-Methylphenyl 3,4,6-tri-O-benzyl-2-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-galactopyranoside is a sophisticated thioglycoside derivative employed in carbohydrate chemistry, specifically in the synthesis of complex oligosaccharides and glycoconjugates. This compound is characterized by a β-D-galactopyranoside core with multiple protective groups that facilitate selective reactivity during glycosylation processes.

Structural Features

• Core Structure: The backbone consists of a β-D-galactopyranoside unit with a thio group at the anomeric position (C1), enhancing its reactivity as a glycosyl donor.
• Protective Groups:
  • Benzyl groups at O-3, O-4, and O-6 provide stability under basic conditions, allowing for controlled reactions without interfering with other functional groups.
  • 9-Fluorenylmethoxycarbonyl (Fmoc) at O-2, which is base-labile and can be selectively removed to activate the hydroxyl for further reactions.

Synthesis Strategy

The synthesis typically involves several key steps:

1. Benzylation: The hydroxyl groups at O-3, O-4, and O-6 are protected by benzylation using benzyl bromide in the presence of a suitable base.
2. Fmoc Protection: The hydroxyl group at O-2 is protected with Fmoc, which can be selectively removed later to allow for further glycosylation reactions.

Physicochemical Properties

• Molecular Formula: Estimated as C₃₆H₃₈O₉S 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