Dimerization of propargyl and homopropargyl 6-azido-6-deoxy-glycosides upon 1,3-dipolar cycloaddition
2008

Dimerization of Glycosides Using Click Reaction

publication Evidence: moderate

Author Information

Author(s): Pietrzik Nikolas, Schmollinger Daniel, Ziegler Thomas

Primary Institution: Institute of Organic Chemistry, University of Tuebingen

Hypothesis

Can glycosides with azido and alkynyl groups undergo dimerization through copper-catalyzed 1,3-dipolar cycloaddition?

Conclusion

The study demonstrates that copper-catalyzed dimerization of certain glycosides can lead to the formation of macrocyclic compounds.

Supporting Evidence

  • The dimerization reaction produced variable yields depending on the conditions.
  • Byproducts were formed during the reaction, complicating product isolation.
  • Microwave irradiation improved reaction speed but also caused decomposition of starting materials.

Takeaway

The researchers found a way to combine sugar molecules using a special chemical reaction, which could help create new materials.

Methodology

Copper-catalyzed 1,3-dipolar cycloaddition of glycosides with azido and alkynyl groups.

Limitations

The yields of dimerization were low to medium and varied based on the sugar moiety and reaction conditions.

Digital Object Identifier (DOI)

10.3762/bjoc.4.30

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