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Related Experiment Videos

Solution-phase library synthesis of furanoses.

Elaine B Krueger1, Thutam P Hopkins, Meghan T Keaney

  • 1Discovery Partners International, ChemRx Division, 385 Oyster Point Boulevard, Suite 1, South San Francisco, California 94080, USA.

Journal of Combinatorial Chemistry
|May 15, 2002
PubMed
Summary

This study presents a novel solution-phase synthesis for creating amido-, urea-, and aminofuranoses. These carbohydrate derivatives were efficiently prepared using reductive amination and acylation techniques, offering new building blocks for chemical synthesis.

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Medicinal Chemistry

Background:

  • Furanose derivatives are important scaffolds in medicinal chemistry.
  • Efficient synthesis of functionalized furanoses is crucial for drug discovery.
  • Existing synthetic routes may lack versatility or scalability.

Purpose of the Study:

  • To develop a versatile solution-phase synthesis for amido-, urea-, and aminofuranoses.
  • To explore the use of reductive amination and acylation for furanose functionalization.
  • To demonstrate the utility of scavenger resins in library synthesis of these compounds.

Main Methods:

  • Reductive amination of alkylated furanose aldehydes with primary and secondary amines using sodium triacetoxyborohydride.
  • Acylation of resulting secondary amines with acid chlorides and isocyanates.

Related Experiment Videos

  • Acid-catalyzed acetal exchange reactions with alcohols.
  • Purification of intermediates and products using functionalized scavenger resins.

    • Main Results:

    • Successful synthesis of secondary and tertiary aminofuranoses.
    • Formation of amidofuranoses and ureafuranoses via acylation.
    • Preparation of mixed acetals from furanose acetonides.
    • Demonstrated efficiency of scavenger resins for purification in library synthesis.

    Conclusions:

    • A robust and adaptable method for synthesizing diverse amido-, urea-, and aminofuranose libraries has been established.
    • The synthetic strategy allows for controlled introduction of various functional groups onto the furanose core.
    • The use of scavenger resins streamlines purification, facilitating high-throughput synthesis.