SYNTHESIS OF FLUORINATED DERIVATIVES OF METHIONINE AND 5'-DEOXY-5'-(METHYLTHIO)-ADENOSINE USING THE McCARTHY TRANSFORMATION OF SULFOXIDES TO α-FLUORO THIOETHERS

Article abstract of DOI:10.1016/S0022-1139(00)80377-2

Treatment of N-acetylmethionine sulfoxide methyl ester with diethylaminosulfur 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.