title: Synthesis and properties of new bolaform and macrocyclic galactose-based surfactants obtained by olefin metathesis.
abstract: A series of galactose-based surfactants with various structures likely to display new interesting properties were synthesized. Four monocatenary surfactants were elaborated by microwave-assisted galactosylation of undecanol or 10-undecenol. These compounds were slightly soluble in water. Their tensioactive properties were determined at 45 degrees C. Olefin metathesis was used to synthesize the two single-chain bolaforms from undec-10-enyl galactopyranosides; two pseudomacrocyclic bolaforms were prepared by grafting two carbamates at O-4 and O-4' sugar positions of the single-chain bolaforms. These four surfactants are insoluble in water and undergo monolayer compression. Cyclization of these bolaforms by olefin metathesis led to macrocyclic surfactant analogues of archaeobacterial membrane components.
authors.affiliation: Université de Limoges, Laboratoire de Chimie des Substances Naturelles, 123 Av. Albert Thomas, F-87060 Limoges, France.
authors.forename: Céline
authors.initials: C
authors.lastname: Satgé
authors.forename: Robert
authors.initials: R
authors.lastname: Granet
authors.forename: Bernard
authors.initials: B
authors.lastname: Verneuil
authors.forename: Yves
authors.initials: Y
authors.lastname: Champavier
authors.forename: Pierre
authors.initials: P
authors.lastname: Krausz
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D005690:Galactose / Q000737:chemistry*; D005697:Galactosides / Q000737:chemistry; D017953:Isocyanates / Q000138:chemical synthesis / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D012995:Solubility; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000475:Alkenes; D005697:Galactosides; D017953:Isocyanates; D047028:Macrocyclic Compounds; D013501:Surface-Active Agents; D005690:Galactose