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

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Journal Article
Monatshefte für Chemie - Chemical, 2011, 142 (3), pp. 297 - 303
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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.
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