4-Methylphenyl 2-O-benzoyl-4-O-benzyl-3-O-(9-fluorenylmethoxycarbonyl)-6-O-levulinoyl-1-thio-β-D-glucopyranoside

4-Methylphenyl 2-O-benzoyl-4-O-benzyl-3-O-(9-fluorenylmethoxycarbonyl)-6-O-levulinoyl-1-thio-β-D-glucopyranoside

4-Methylphenyl 2-O-benzoyl-4-O-benzyl-3-O-(9-fluorenylmethoxycarbonyl)-6-O-levulinoyl-1-thio-β-D-glucopyranoside is a strategically protected thioglycoside designed for controlled glycosylation in complex carbohydrate synthesis. This compound combines orthogonal protecting groups to enable precise sequential deprotection during oligosaccharide assembly.

Structural Features

Core framework:

• β-D-glucopyranose ring with a 4-methylphenylthio group at the anomeric position (C1), forming a stable thioglycoside donor for glycosidic bond formation.

Protection pattern:

Key Properties

• Molecular formula: C₄₈H₄₅NO₉S (estimated based on substituent masses)
• Molecular weight: ~836.0 g/mol
• Physical form: White crystalline solid (typical for protected carbohydrates)
• Reactivity:
  • Activatable via thiophilic promoters (e.g., NIS/TfOH) for glycosylation
  • Electron-withdrawing benzoyl group moderates donor reactivity

Synthetic Utility

1. Orthogonal deprotection sequence:
   • Step 1: Fmoc removal at C3 (base) without affecting other groups
   • Step 2: Levulinoyl cleavage at C6 (mild acid)
   • Step 3: Benzoyl removal at C2 (alkaline conditions)
   • Step 4: Final benzyl deprotection at C4 (H₂/Pd-C)
2. Solid-phase compatibility:
   • Fmoc group enables use in automated synthesis platforms
   • Levulinoyl permits temporary protection during chain elongation
3. Branch-selective functionalization:
   • Exposed C3/C6 hydroxyls after deprotection allow site-specific modifications

Applications

• Glycoconjugate vaccine development: Controlled exposure of hydroxyl groups for antigen coupling
• Glycosidase inhibitor synthesis: Serves as a protected glucose scaffold for analog design
• Dendrimer construction: Enables iterative branching through sequential deprotection

Stability Profile

The compound exemplifies advanced carbohydrate engineering, merging traditional protecting groups (benzyl, benzoyl) with modern orthogonal motifs (Fmoc, levulinoyl) for precision in glycan assembly. Its design allows compatibility with both solution-phase and solid-phase synthesis methodologies.

Citations:

1. https://synthose.com/products/ML822
2. https://patents.google.com/patent/WO2019206853A1/en
3. https://synthose.com/products/MG340
4. https://patentimages.storage.googleapis.com/c4/a8/90/85cbb5f7ecd198/US7511022.pdf
5. https://pubchem.ncbi.nlm.nih.gov/compound/1-Benzyl-4-_4-methylphenyl_-1h-1_2_3-triazole
6. https://www.bocsci.com/product/4-methylphenyl-2-o-benzoyl-3-4-di-o-benzyl-6-o-9-fluorenylmethoxycarbonyl-339431.html
7. https://patents.google.com/patent/WO2018053215A1/en
8. https://www.chemicalbook.com/ProdSupplierGWCB29036383_EN.htm