Stereoselective synthesis of 2-S-ethyl(phenyl)-2-thio-β-glucopyranosides via 1,2-migration and concurrent glycosidation of ethyl(phenyl) 2,3-orthoester-1-thio-α-mannopyranosides Original Research Article

1,2-Migration and concurrent glycosidation of ethyl(phenyl) 2,3-orthoester-1-thio-α-d- and l-mannopyranosides under the action of TMSOTf readily afforded the corresponding 2-S-ethyl(phenyl)-2-thio-β-glucopyranosides, ready precursors to 2-deoxy-arabino-hexopyranosides (2-deoxy-β-glucopyranosides).