Linear and cyclic C-glycosides as surfactants

Abstract

Carbohydrate-based surfactants have long been of interest due to their desirable performance properties and their potential to be derived from renewable feedstocks. Although most carbohydrate based surfactants utilize an O-glycosidic linkage, recent advances in carbohydrate C–C bond formation allows for the facile synthesis of new classes of carbohydrate-based surfactants on a C-glycosidic linkage. Herein is described an approach that can generate a wide variety of C-glycoside surfactants in moderate to very good yield by treating the nonulose C-glycoside intermediate first described by Lubineau et al. with pyrrolidine in the presence of an alkyl aldehyde. Depending on the stoichiometry and reaction conditions, this chemistry will result in either a linear enoneC-glycoside, or a cyclohexenoneC-glycoside, both of which demonstrate interesting surfactant properties. Further, the linear enone series can be photochemically modified or reacted with other alkyl aldehydes to generate additional analogs.