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CS-W001157 4
Total: USD 88.00

α-D-glucopyranosyl fluoride

  • CAS No. 2106-10-7

  • Cat. No. CS-0098112
  • Purity≥95%
  • MDL No.MFCD00132903

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

α-D-glucopyranosyl fluoride|CS-0098112

Structure of 2106-10-7

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General Information

  • CAS No. 2106-10-7
  • Cat. No. CS-0098112
  • Purity ≥95%
  • MDL No. MFCD00132903
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₁₁FO₅
  • Molecular Weight 182.15
  • Synonym(s) glucosyl fluoride
  • SMILES O[C@H]1[C@H](O)[C@@H](CO)O[C@H](F)[C@@H]1O

Description

α-D-Glucopyranosyl fluoride serves as a potent glycosylation agent, enabling selective C-glycoside formation under mild conditions. This stable fluorinated glycosyl donor features a reactive anomeric fluoride that facilitates efficient coupling with nucleophiles. Its bench-stable nature and compatibility with diverse substrates streamline access to complex carbohydrate architectures in synthetic and biological contexts.

Application

α-D-Glucopyranosyl fluoride serves as a stable, bench-ready glycosyl donor enabling efficient α-selective glycosylation reactions. Its fluorine substituent provides excellent leaving group ability while maintaining chemical stability under ambient conditions. Functions reliably in standard glycosylation protocols, offering high stereoselectivity and compatibility with diverse acceptor alcohols, making it a practical choice for constructing glycosidic linkages in carbohydrate synthesis and natural product derivatization.

Synthesis

  • Route1
    • null|null
      439-03-2
    • ~98%
    • In-stock
      α-D-glucopyranosyl fluoride|CS-0098112
      2106-10-7

    References

    • Steinmann, Andreas; Thimm, Julian; Matwiejuk, Martin; Thiem, Joachim Macromolecules, 2010 , vol. 43, # 8 p. 3606 - 3612
  • Route2
    • (2S,3R,4S,5S,6R)-2-(2,4-dinitrophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol|CS-0516869
      25775-97-7
    • ~%
    • In-stock
      α-D-glucopyranosyl fluoride|CS-0098112
      2106-10-7

    References

    • Zechel; Reid; Nashiru; Mayer; Stoll; Jakeman; Warren; Withers Journal of the American Chemical Society, 2001 , vol. 123, # 18 p. 4350 - 4351
  • Route3
    • null|null
      2280-44-6
    • ~%
    • In-stock
      α-D-glucopyranosyl fluoride|CS-0098112
      2106-10-7

    References

    • Defaye, Jacques; Gadelle, Andree Carbohydrate Research, 1982 , vol. 110, p. 217 - 228

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   90.15
  • LogP   -2.2442
  • H_Acceptors   5
  • H_Donors   4
  • Rotatable_Bonds   1

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