Approaches to the Synthesis of Perfluoroalkyl‐Modified Carbohydrates and Derivatives: thiosugars, iminosugars, and tetrahydro(thio)pyrans

UHRIG, MARÍA LAURA; MORA FLORES, ERWIN W.; POSTIGO, AL

CHEMISTRY-A EUROPEAN JOURNAL

WILEY-V C H VERLAG GMBH

Año: 2021 vol. 27 p. 7813 - 7825

0947-6539

10.1002/chem.202005229Fluoroalkyl-substituted carbohydrates play relevant roles in diverse areas such as supramolecular chemistry, glycoconjugation, liquid crystals and surfactants, with direct applications as wetting, antifreeze, and coating agents. In the light of these promising properties, new methodologies for the late-stage incorporation of fluoroalkyl RF groups into carbohydrates and derivatives are herein presented as they became relevant to the synthetic carbohydrate community. Previously reviewed protocols for the installation of RF groups onto carbohydrates and derivatives will be succinctly summarized in the light of the new achievements. Fluoroalkyl-substituted iminosugars, on the other hand, are also interesting glycomimetic derivatives with prominent roles as glycosidases and glycosyltransferases inhibitors, as has recently been demonstrated. Also, they positively contribute to the study of sugar-protein interactions and enzyme mechanisms. New advances in the syntheses of fluoroalkyl-substituted iminosugars will also be presented here.