Synthesis of N-Propargyl Iminosugar Scaffolds for Compound Library Generation using Click Chemistry

Brendan L. Wilkinson; Laurent F. Bornaghi; Marie Lopez; Peter C. Healy; Sally-Ann Poulsen; Todd A. Houston

doi:10.1071/CH09426

RESEARCH ARTICLE

Synthesis of N-Propargyl Iminosugar Scaffolds for Compound Library Generation using Click Chemistry

Brendan L. Wilkinson ^A , Laurent F. Bornaghi ^A , Marie Lopez ^A , Peter C. Healy ^A , Sally-Ann Poulsen ^A ^C and Todd A. Houston ^B ^C

+ Author Affiliations

- Author Affiliations

^A Eskitis Institute, Griffith University, Nathan, Qld 4111, Australia.

^B Institute for Glycomics, Gold Coast Campus, Griffith University, Qld 4222, Australia.

^C Corresponding authors. Email: s.poulsen@griffith.edu.au; t.houston@griffith.edu.au

Australian Journal of Chemistry 63(5) 821-829 https://doi.org/10.1071/CH09426
Submitted: 6 August 2009 Accepted: 24 September 2009 Published: 21 May 2010

Abstract

We have developed an efficient synthesis of N-propargyl iminosugars for use in diversity-oriented library development. Through a common, crystalline intermediate both piperidine and azepane scaffolds can be prepared with an alkyne functional group, allowing for further elaboration through reaction with azides.

Acknowledgements

We wish to thank the Eskitis Institute for Cell and Molecular Therapies and the Institute of Glycomics for support. We are grateful to Prof. Paul Bernhardt, the University of Queensland, for the collection of X-ray data for compound 1.

References

Synthesis of N-Propargyl Iminosugar Scaffolds for Compound Library Generation using Click Chemistry

Abstract

Acknowledgements

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