New Insights into the Reactivity of 2-Halo-Glycals. Synthesis of Novel Iodinated Oand S-Glycosides

Abstract

<jats:p>&lt;p&gt;&lt;i&gt;This is the first report on the Ferrier rearrangement of 2-halo-glycals with S-nucleophiles. We present herein the selective synthesis of new 2-iodo-2,3-unsaturated O- and S-glycosides. We obtained in good yields and high anomeric selectivity &lt;/i&gt;&lt;i&gt;a&lt;/i&gt;&lt;i&gt;-glycosydes. As a particular behaviour, we also describe heteroaromatic thio sugar derivatives were the C3 addition was performed in an alternative mechanism. A complete structure and conformation analysis by NMR was also presented. &lt;/i&gt;&lt;/p&gt;</jats:p>