Characterization and interconversions of 2-S-ethyl-2-thio-d-mannose diethyl dithioacetal and the facile epimerization of 2-thio-d-mannopyranose derivatives
3, 4, 5, 6-Tetra-O-benzoyl-d-glucose diethyl dithioacetal (2) reacts with ethanethiol under acidic conditions to afford 3, 4, 5, 6-tetra-O-benzoyl-2-S-ethyl-2-thio-d-mannose (3), the stereochemistry at C-2 of which has been assigned by chemical conversions on its debenzoylated derivative, the crystalline 2-S-ethyl-2-thio-d-mannose diethyl dithioacetal (4). In the presence of mercuric chloride (1.1 molar equiv), 4 is converted into crystalline ethyl ...