N??Thiocarbonyl Iminosugars: Synthesis and Evaluation of Castanospermine Analogues Bearing Oxazole??2 (3H)??thione Moieties

…, EM Sánchez??Fernández, C Ortiz Mellet…

Index: Silva, Sandrina; Sanchez-Fernandez, Elena M.; Ortiz Mellet, Carmen; Tatibouet, Arnaud; Pilar Rauter, Amelia; Rollin, Patrick European Journal of Organic Chemistry, 2013 , # 35 p. 7941 - 7951

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Abstract

Abstract A straightforward and efficient synthetic route to a new class of glycosidase inhibitors containing an oxazole-2 (3H)-thione moiety has been devised. The approach involves the formation of α-hydroxy ketones, which, after condensation with thiocyanic acid, leads to the formation of the heterocycle. By exploiting the ability of the nitrogen atom of oxazoline-2-thione precursors to act as nucleophiles in intramolecular addition, ...