jo5b02853_si_001.pdf (3.66 MB)
Reaction of Glyconitriles with Organometallic Reagents: Access to Acyl β‑C‑Glycosides
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 GuillarmeA 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.