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

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The stereocontrolled TMSOTf-ring opening of 1,6-anhydrosugars with TMSCN leading to glycosyl cyanides is presented as well as an application to the straightforward synthesis of a conformationally-constrained analogue of 1-cyano D-glucal.


Abstract

We 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.

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