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

Authors

Alison T. UngFollow
Stephen G. Pyne, University of WollongongFollow
Brian W. Skelton
A White
G R. Jeoffreys

RIS ID

44850

Publication Details

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.

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. Copyright 2011 Springer-Verlag.