Synthesis of 2-Acetyl-5-(1,2,3,4,5,6-hexahydroxyhexyl)thiazoles. -The synthesis of two diastereomers of the title compound involves the coupling of 5-lithiated 2-(1,1-dimethoxyethyl)thiazole (VI) with a Weinreb amide (V) derived from gluconolacetone, followed by asymmetric reduction of the ketone functionality. -(UNG*, A. T.; PYNE, S. G.; JEOFFREYS, G. R.; SKELTON, B. W.; WHITE, A. H.; Monatsh. Chem. 142 (2011) 3, 297-303, http://dx.
4-tetrahydroxybutyl)imidazole. -Reactions between dimethoxyketals of thiazoles and sugar lactones [cf. (I) + (II)] are the starting steps in the preparation of a series of title compounds such as (V)-(VIII), analogues of THI (IX). Preliminary studies reveal that (V) is as active as (IX), whereas (VII) shows a slightly higher activity. -(JEOFFREYS, GEORGE R.; UNG, ALISON T.; PYNE, STEPHEN G.; SKELTON, BRIAN W.; WHITE, ALLAN H.; J.
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