Carbohydrate research

Characterization and interconversions of 2-S-ethyl-2-thio-d-mannose diethyl dithioacetal and the facile epimerization of 2-thio-d-mannopyranose derivatives

D Horton, P Norris, B Berrang

Index: Horton, Derek; Norris, Peter; Berrang, Bertold Carbohydrate Research, 1996 , vol. 283, p. 53 - 71

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Citation Number: 4

Abstract

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 ...