Synthesis of fluorinated derivatives of methionine and 5′-deoxy-5′-(methylthio)-adenosine using the mccarthy transformation of sulfoxides to α-fluoro thioethers

Abstract Treatment of N-acetylmethionine sulfoxide methyl ester with diethylamino- sulfur trifluoride (DAST) or dimethylaminosulfur trifluoride (meDAST) yielded N-acetyl-S-(monofluoromethyl)homocysteine methyl ester as the sole fluorinated product. In contrast, treatment of 2′,3′-di-O-acetyl-5′-(methylthio)adenosine sulfoxide with DAST or meDAST unexpectedly produced three novel fluorinated products.