Linear and cyclic C-glycosides as surfactants

Autor:	Patrick Foley, Julie B. Zimmerman, Anthony Phimphachanh, Paul T. Anastas, Evan S. Beach
Rok vydání:	2011
Předmět:	chemistry.chemical_classification Cyclic compound Chemistry Pollution Chemical synthesis Aldehyde Pyrrolidine chemistry.chemical_compound Chemical bond Yield (chemistry) Environmental Chemistry Organic chemistry Enone Alkyl
Zdroj:	Green Chem.. 13:321-325
ISSN:	1463-9270 1463-9262
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b2c2c0d6989096799c5fb374bd4bc364 https://doi.org/10.1039/c0gc00407c Zobrazit plný text záznamu