Inositol is a non-classical carbohydrate that exists in both prokaryotes and eukaryotes with functions in signaling and anchoring molecules to cell surfaces.  Due to the challenges of studying glycoconjugates using traditional biochemical techniques, azido inositol analogues may have value as bioorthogonal chemical reporters for studying inositol-containing biomolecules in various systems.  However, the synthesis of these compounds is challenging due to inositol’s internal plane of symmetry and the need to differentiate six secondary hydroxyl groups.  In this study, we report progress on a de novo chemical synthesis of 3-azido-3-deoxy-<i>myo</i>-inositol starting from a simple precursor, methyl 2-azido-2-deoxy-α-D-glucopyranoside.<br/>

De Novo chemical synthesis of 3-azido-3-deoxy-myo-inositol via Ferrier rearrangement

253rd National Meeting (2017)

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