Stereoselective synthesis of iminosugar-C-glycosides through addition of organometallic reagents to N-tert-butanesulfinyl glycosylamines: A comprehensive study
Synthèse stéréosélective d'iminosucre-C-glycosides par addition de réactifs organométalliques sur des N-tert-butanesulfinyl glycosylamines
Résumé
A comprehensive study of the preparation and reactivity of N-tert-butanesulfinyl glycosylamines with simple Grignard and organo lithium reagents in batch vs. continuous flow chemistry is reported. As they readily react as latent imine equivalents with a variety of carbon nucleophiles, these carbohydrate derivatives constitute very useful precursors for the diastereoselective synthesis of bioactive compounds such as iminosugar-C-glycosides. A hybrid protocol, involving the addition of benzylmagnesium chloride to a (SR)arabinofuranosylamine substrate in flow, at room temperature, combined with a cyclization protocol in batch is also described for the first time. Of note, this semi-continuous flow process shortens the synthesis of imino-C-glycoside scaffolds to a single workday
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