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Synthesis of 2-acetyl-5-(1,2,3,4,5,6-hexahydroxyhexyl)thiazoles

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Abstract

The syntheses of two diastereoisomers of 2-acetyl-5-(1,2,3,4,5,6-hexahydroxyhexyl)thiazole are reported. The synthesis of these diastereoisomers involved the coupling of 5-metallated 2-(1,1-dimethoxyethyl)thiazole with a Weinreb amide derived from δ-gluconolactone, followed by asymmetric reduction of the ketone thus prepared. The stereochemistries and structures of some key compounds were determined by single-crystal X-ray structural analysis.

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Acknowledgments

We thank Johnson and Johnson Research Pty. Limited, Sydney, and the University of Wollongong for supporting this research, the Australian Research Council for an APA(I) scholarship to GRJ and Prof. Dennis Wade and Dr. David Atkins for encouragement and support.

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Authors and Affiliations

  1. Department of Chemistry and Forensic Science, University of Technology, Sydney, P.O. Box 123, Broadway, Sydney, NSW, 2007, Australia

    Alison T. Ung

  2. School of Chemistry, University of Wollongong, Wollongong, NSW, 2522, Australia

    Stephen G. Pyne & George R. Jeoffreys

  3. Department of Chemistry, University of Western Australia, Nedlands, WA, 6907, Australia

    Brian W. Skelton & Allan H. White

Authors
  1. Alison T. Ung
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  2. Stephen G. Pyne
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  3. George R. Jeoffreys
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  4. Brian W. Skelton
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  5. Allan H. White
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Correspondence to Alison T. Ung.

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Ung, A.T., Pyne, S.G., Jeoffreys, G.R. et al. Synthesis of 2-acetyl-5-(1,2,3,4,5,6-hexahydroxyhexyl)thiazoles. Monatsh Chem 142, 297–303 (2011). https://doi.org/10.1007/s00706-011-0448-z

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  • DOI: https://doi.org/10.1007/s00706-011-0448-z

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