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

Journal Article


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 d-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. © 2011 Springer-Verlag.

UOW Authors


  •   Ung, Alison T. (external author)
  •   Pyne, Stephen
  •   Jeoffreys, G R. (external author)
  •   Skelton, Brian W. (external author)
  •   White, Allan H. (external author)

Publication Date


  • 2011

Citation


  • Ung, A. T., Pyne, S. G., Jeoffreys, G. R., Skelton, B. W. & White, A. H. (2011). Synthesis of 2-acetyl-5-(1,2,3,4,5,6-hexahydroxyhexyl)thiazoles. Monatshefte fur Chemie, 142 (3), 297-303.

Scopus Eid


  • 2-s2.0-79955803280

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/3604

Number Of Pages


  • 6

Start Page


  • 297

End Page


  • 303

Volume


  • 142

Issue


  • 3

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 d-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. © 2011 Springer-Verlag.

UOW Authors


  •   Ung, Alison T. (external author)
  •   Pyne, Stephen
  •   Jeoffreys, G R. (external author)
  •   Skelton, Brian W. (external author)
  •   White, Allan H. (external author)

Publication Date


  • 2011

Citation


  • Ung, A. T., Pyne, S. G., Jeoffreys, G. R., Skelton, B. W. & White, A. H. (2011). Synthesis of 2-acetyl-5-(1,2,3,4,5,6-hexahydroxyhexyl)thiazoles. Monatshefte fur Chemie, 142 (3), 297-303.

Scopus Eid


  • 2-s2.0-79955803280

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/3604

Number Of Pages


  • 6

Start Page


  • 297

End Page


  • 303

Volume


  • 142

Issue


  • 3