Stereoselective Synthesis of Glycosyl Cyanides by TMSOTf‐Mediated Ring Opening of 1,6‐Anhydro Sugars

Abstract

AbstractWe describe herein a convenient access to glycosyl cyanides by way of TMSCN ring opening of 1,6‐anhydro sugars mediated by TMSOTf with modest to high stereocontrol in the D‐gluco, D‐galacto and D‐manno series. The reaction is tolerant to various functional groups including free alcohols, alkenes and terminal alkynes. The straightforward synthesis of a constrained analogue of 1‐cyano‐D‐glucal with a 3,6‐anhydro sugar framework is presented to illustrate the interest of the TMSCN ring‐opening reaction.