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Issue 2, 2011
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Linear and cyclic C-glycosides as surfactants

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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.

Graphical abstract: Linear and cyclic C-glycosides as surfactants

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The article was received on 06 Aug 2010, accepted on 22 Nov 2010 and first published on 13 Dec 2010

Article type: Paper
DOI: 10.1039/C0GC00407C
Green Chem., 2011,13, 321-325

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    Linear and cyclic C-glycosides as surfactants

    P. M. Foley, A. Phimphachanh, E. S. Beach, J. B. Zimmerman and P. T. Anastas, Green Chem., 2011, 13, 321
    DOI: 10.1039/C0GC00407C

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