The Synthesis of Fluorinated Carbohydrates Using Sulfuryl Fluoride as the Deoxyfluorination Reagent

Abstract

Fluorination of carbohydrates has been one of the strategies to increase their enzymatic and chemical stabilities and reduce their hydrophilicities, making this modification attractive for drug discovery purposes. The synthesis of monofluorinated carbohydrates was achieved under mild conditions by using SO2F2 as the deoxyfluorination reagent in the presence of a base without extra fluoride additives. This method features low toxicity, easy availability, low cost, and high efficiency and can be subjected to diverse sugar units.