Oxidative transformations of 6-trifluoromethyl-2H-thiopyran as a route to fluoro-containing thiopyranosides

• DOI: 10.1016/j.tetlet.2011.09.080
• Publication Date: 2011-09-22T00:40:44Z
• Authors: Sergiy A. Siry; Vadim M. Timoshenko
• Keywords: 01 natural sciences; 0104 chemical sciences

Abstract The synthesis of cis- and trans -6-(trifluoromethyl)-3,4-dihydro-2 H -thiopyran-3,4-diols from 6-(trifluoromethyl)-2 H -thiopyran via an OsO 4 -catalysed dihydroxylation and bromohydroxylation–alkaline hydrolysis sequence is described. Acetylation of the diols followed by S -oxidation affords the corresponding cis- and trans -3,4-diacetoxy-6-(trifluoromethyl)-3,4-dihydro-2 H -thiopyran S-oxides which reacted with acetic anhydride and boron trifluoride diethyl ether complex by an additive Pummerer pathway giving tetraacetyl derivatives of trifluoromethyl-containing thiopyranoses.