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 enone C-glycoside, or a cyclohexenone C-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.This journal is

Chemoselective Reactions for the Synthesis of Glycoconjugates from Unprotected Carbohydrates

“…Later, in 2011, Anastas et al. studied the condensation of β‐C‐glycosyl propanones with aliphatic aldehydes in the presence of pyrrolidine as catalyst to afford glycosidic surfactants (Scheme ) . When the reactions were conducted with 1 equivalent of the aldehyde in a mixture of DMF and heptane, the linear enones were obtained as the main products in reasonable yields.…”

“… Aldol condensation of 1‐(β‐ d ‐glucopyranosyl)propan‐2‐one with an aliphatic aldehyde to afford glycoside surfactants . a) pyrrolidine, DMF/heptane (60 %).…”

Surfactants from Itaconic Acid: Physicochemical Properties and Assessment of the Synthetic Strategies

“…Routes B1 and B2 exploit dimethylitaconate 9 that is obtained from IA using MeOH-BF 3 and H 2 SO 4 , respectively. Otherwise, the methylation of the carboxylic acid functionality of 1a and 2a in route B3 has been carried out with dimethyl carbonate (DMC) in the presence of …”

Synthesis and use of new C-glycosyl bicyclic lactones

“…4 C-Glycosyl derivatives can also show interesting properties in the field of surfactants. 5 Apart from aromatic fused systems arising from C-glycosyl ortho-carboxy arenes, such as the naturally occurring bergenin and its analogues 6 only rare examples of simple lactones with a C-propanoyl appendage have been previously reported, 7 though not with the idea to serve as scaffolds. Some of them have been used as intermediates towards complex structures by carbon-carbon bond formation on the carbonyl group of the lactone, either by reaction of an …”