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

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

4-Methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-galactopyranoside is a synthetic thioglycoside derivative designed for controlled reactivity in carbohydrate chemistry. Its structure features a β-D-galactopyranoside backbone with strategically placed protective groups to enable selective deprotection during oligosaccharide synthesis.

Structural Characteristics

• Core scaffold: β-D-galactopyranoside with a 4-methylphenyl thio-group at the anomeric position (C1).
• Protective group arrangement:
  • Benzoyl at O-2 (acid-sensitive protection).
  • Benzyl groups at O-4 and O-6 (stable under basic conditions).
  • 9-Fluorenylmethoxycarbonyl (Fmoc) at O-3 (base-labile, allowing orthogonal deprotection).

Applications

• Acts as a glycosidase inhibitor, making it valuable for studying metabolic disorders like diabetes and cancer.
• Used in glycoconjugate synthesis for site-specific modifications in glycan assembly.

Physicochemical Properties

• Molecular formula: Estimated as C₅₀H₅₀O₈S (based on substituent analysis).
• Appearance: Likely a white crystalline solid (similar to analogs in search results).
• Solubility: Compatible with polar aprotic solvents like DMSO, DMF, or DCM.

Synthesis Strategy

Typical steps include:

1. Sequential installation of benzyl, benzoyl, and Fmoc groups via selective protection reactions.
2. Thio-glycoside formation using 4-methylthiophenol.

Safety and Handling

• Classified as non-hazardous under standard GHS guidelines.
• Recommended storage at 0–8°C for stability.

This compound exemplifies the precision of modern glycosylation strategies, balancing protective group orthogonality and reactivity for biomedical research applications.

Citations:

1. https://glycomindsynth.com/product_detail/517/Monosaccharide
2. https://www.chemicalbook.com/ProdSupplierGWCB29036383_EN.htm
3. https://synthose.com/products/ML822
4. https://www.sigmaaldrich.com/FR/fr/search/4-methoxy-benzyl-isocyanate?focus=papers&page=1&perpage=30&sort=relevance&term=4-methoxy+benzyl+isocyanate&type=citation_search
5. https://synthose.com/products/MG340
6. https://www.bocsci.com/product/4-methylphenyl-2-o-benzoyl-3-4-di-o-benzyl-6-o-9-fluorenylmethoxycarbonyl-339431.html
7. https://pubchem.ncbi.nlm.nih.gov/compound/72981508
8. https://labshake.com/product/399e6a13-22b5-482b-aa76-bac0621fa7db/-4-Methylphenyl-2-O-benzoyl-4-6-di-O-benzyl-3-O–9-fluorenylmethoxycarbonyl–1-thio-%CE%B2-D-galactopyranoside