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

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

4-Methylphenyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-galactopyranoside is a complex thioglycoside derivative used in carbohydrate chemistry and glycoconjugate synthesis. This compound features multiple protective groups strategically placed to enable controlled reactivity during oligosaccharide assembly.

Structural Features

• Core structure: β-D-galactopyranoside backbone with a 4-methylphenyl thio-group at the anomeric position (C1).
• Protective groups:
  • Benzoyl at O-2 for acid-labile protection.
  • Benzyl groups at O-3 and O-4 for stability under basic conditions.
  • 9-Fluorenylmethoxycarbonyl (Fmoc) at O-6, a base-labile protecting group allowing selective deprotection.

Synthesis and Applications

• Synthesis: Typically involves sequential protection steps:
  1. Benzoylation of O-2.
  2. Benzylation of O-3 and O-4.
  3. Fmoc installation at O-6.
  4. Thio-glycoside formation via reaction with 4-methylthiophenol.
• Applications:
  • Key intermediate in synthesizing glycosylated biomolecules.
  • Enables site-specific modifications in glycan assembly due to orthogonal protecting groups.

Physicochemical Properties

• Molecular formula: Likely C₅₀H₅₀O₈S (estimated based on similar structures).
• Appearance: White crystalline solid.
• Solubility: Soluble in DMSO, DCM, and DMF.
• Storage: Recommended at -20°C for long-term stability.

Safety and Handling

• Classified as non-hazardous under GHS guidelines.
• Standard laboratory precautions apply for organic compounds (gloves, ventilation).

This compound’s design highlights the precision required in glycan engineering, balancing protective group compatibility and reactivity for targeted biochemical applications.

Citations:

1. https://glycomindsynth.com/product_detail/517/Monosaccharide
2. https://www.pharmaffiliates.com/en/2088577-19-7-4-methylphenyl-2-o-benzoyl-3-6-di-o-benzyl-4-o-9-fluorenylmethoxycarbonyl-1-thio-beta-d-galactopyranoside-pa270026106.html
3. https://www.chemicalbook.com/ProdSupplierGWCB29036383_EN.htm
4. https://www.bocsci.com/product/4-methylphenyl-2-o-benzoyl-3-6-di-o-benzyl-4-cas-2088577-19-7-339099.html
5. https://pubchem.ncbi.nlm.nih.gov/compound/1326804-93-6
6. https://www.chemicalbook.com/ProductChemicalPropertiesCB09036329_EN.htm
7. https://synthose.com/products/ML822
8. https://www.pharmaffiliates.com/en/parentapi/miscellaneous-impurities?page=289
9. https://synthose.com/products/MG340