American Chemical Society
jo5b02853_si_001.pdf (3.66 MB)

Reaction of Glyconitriles with Organometallic Reagents: Access to Acyl β‑C‑Glycosides

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journal contribution
posted on 2016-02-29, 00:00 authored by Nicolas E. S. Guisot, Idriss Ella Obame, Prathap Ireddy, Arnaud Nourry, Christine Saluzzo, Gilles Dujardin, Didier Dubreuil, Muriel Pipelier, Stéphane Guillarme
A new strategy for the synthesis of acyl β-C-glycosides is described. The reactivity of glyconitriles toward organometallic reagents such as organomagnesium or organolithium derivatives was studied, affording acyl β-C-glycosides in moderate to good yields. In this study, glycal formation was efficiently prevented by deprotonating the hydroxyl group in position 2 of the glyconitriles during the process.