Synthesis and properties of new bolaform and macrocyclic galactose-based surfactants obtained by olefin metathesis.
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.
Satgé
Céline
C
Université de Limoges, Laboratoire de Chimie des Substances Naturelles, 123 Av. Albert Thomas, F-87060 Limoges, France.
Granet
Robert
R
Verneuil
Bernard
B
Champavier
Yves
Y
Krausz
Pierre
P
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*
D000475:Alkenes; D005697:Galactosides; D017953:Isocyanates; D047028:Macrocyclic Compounds; D013501:Surface-Active Agents; D005690:Galactose