Oxidative transformations of 6-trifluoromethyl-2H-thiopyran as a route to fluoro-containing thiopyranosides |
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Authors: | Sergiy A. SiryVadim M. Timoshenko |
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Affiliation: | Institute of Organic Chemistry, NAS of Ukraine, Murmanska 5, 02094 Kyiv, Ukraine |
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Abstract: | The synthesis of cis- and trans-6-(trifluoromethyl)-3,4-dihydro-2H-thiopyran-3,4-diols from 6-(trifluoromethyl)-2H-thiopyran via an OsO4-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-2H-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. |
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Keywords: | Trifluoromethyl Thiopyran Dihydroxylation Bromohydroxylation Additive Pummerer reaction |
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