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CS-W001157 4
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2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate

  • CAS No. 74808-09-6

  • Cat. No. CS-0098105
  • Molecule weight685.03
  • Purity≥95%
  • MDL No.MFCD03427010

*For research and further manufacturing use only, not for direct human use.

2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate|CS-0098105

Structure of 74808-09-6

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General Information

  • CAS No. 74808-09-6
  • Cat. No. CS-0098105
  • Purity ≥95%
  • MDL No. MFCD03427010
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₃₆H₃₆Cl₃NO₆
  • Molecular Weight 685.03
  • Synonym(s) 2,3,4,6-tetra-o-benzyl-α-d-glucopyranosyl trichloroacetimidate
  • SMILES N=C(C(Cl)(Cl)Cl)O[C@@H]1[C@H](OCC2=CC=CC=C2)[C@@H](OCC3=CC=CC=C3)[C@H](OCC4=CC=CC=C4)[C@@H](COCC5=CC=CC=C5)O1

Description

This tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate serves as a highly effective glycosyl donor for stereoselective glycosylation reactions. The benzylated hydroxyls enhance solubility and stability, while the trichloroacetimidate group enables rapid activation under mild conditions. This combination facilitates efficient, high-yielding coupling in complex oligosaccharide synthesis.

Application

2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate serves as a highly reliable glycosyl donor in automated and manual glycosylation protocols. Its benzyl-protected sugar core ensures excellent bench stability and compatibility with a broad range of acceptor alcohols. The trichloroacetimidate functionality enables controlled activation under mild conditions, facilitating stereoselective α-glycoside formation. This reagent is widely employed in the synthesis of complex oligosaccharides and glycoconjugates, particularly in medicinal chemistry and carbohydrate-based vaccine development.

Synthesis

  • Route1
    • In-stock
      2,3,4,6-Tetra-O-benzyl-D-glucopyranose|CS-W011467
      4132-28-9
    • null|null
      545-06-2
    • ~96%
    • In-stock
      2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate|CS-0098105
      74808-09-6

    References

    • Ali, Asif; Vishwakarma, Ram A. Tetrahedron, 2010 , vol. 66, # 24 p. 4357 - 4369
  • Route2
    • null|null
      51023-63-3
    • ~%
    • In-stock
      2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate|CS-0098105
      74808-09-6

    References

    • Journal of Medicinal Chemistry, , vol. 29, # 10 p. 1945 - 1952
  • Route3
    • null|null
      100-44-7
    • ~%
    • In-stock
      2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate|CS-0098105
      74808-09-6

    References

    • Journal of Medicinal Chemistry, , vol. 29, # 10 p. 1945 - 1952

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   79.23
  • LogP   8.04837
  • H_Acceptors   7
  • H_Donors   1
  • Rotatable_Bonds   14

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