Fluorine-Containing Carbohydrates

Fluorine-containing carbohydrates are used as biological probes to study various biological processes (especially carbohydrate-protein interactions). ¹ The fluorine substituent is the optimal bioisostere of the hydroxy group because of its size, stability, and its ability to accept hydrogen-bond. ² Despite increased interest in the preparation of fluoro sugars, the introduction of the fluorine atom into some sugar moieties can still be a challenge. ³ Diethylaminosulfur trifluoride (DAST)-mediated fluorination and the two-step nucleophilic substitution of leaving groups with a fluoride-ion are the most common approaches to fluorinated carbohydrates. In addition, linear de novo methodologies are also used for the preparation of fluorine-containing carbohydrates but are less attractive due to their longer synthetic sequences. ⁴ In this context, the pioneering work of Linclau’s group for the synthesis of heavily fluorinated monosaccharides as substrates for enzymatic reactions is also worth noting. ⁵