A one-pot synthesis of novel N,N-dialkyl-S-glycosylsulfenamides Original Research Article

An efficient new entry into N,N-dialkyl-S-glycosylsulfenamides is reported. The reaction of bis-activated alkyl halides in the presence of a secondary amine base with glycosylic S-acetyl derivatives (1-S-acetyl-1-thioaldoses or 2-S-acetyl-2-thioketoses) results in the formation of novel carbohydrate sulfenamides. These new carbohydrate-based sulfenamides may provide useful derivatives with biological activity, as well as provide reactive carbohydrate sulfenylating agents.