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

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Cat Number: A12-GD-2026
4-Methylphenyl 2,3-di-O-benzoyl-4-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-1-thio-ß-D-glucopyranoside; > 95%
CAS: 2796179-44-5
Mr: 806.93 g/mol
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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

 

2. MSDS

3. Tech Data Sheets/Manuals

Size

1 G, 10 G, 30G

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