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

J Org Chem. 2016 Mar 18;81(6):2364-71. doi: 10.1021/acs.joc.5b02853. Epub 2016 Mar 9.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't