Synthesis of novel bis (glycosyl) ethers as bolaamphiphile surfactants

We have synthesized new bolaamphiphile carbohydrate derivatives having general structures AO(CH2)nOB or [AO(CH2)n]2C(OH)R. The hydrophilic heads A and B (identical or different) are d-glucose, d-galactose, xylitol, or their respective protected derivatives, and R is an alkyl chain. The carbohydrate units A and B are condensed in the first step as di-O-isopropylidene derivatives with either α,ω-dibromo- or dimesyl-alkanes in the presence of powdered KOH in 9:1 or 4:1 toluene-Me2SO. Appropriate choice of either selective or total deprotection of acetal groups and either regioselective esterification or regiospecific etherification allows modulation of either the hydrophilic or the lipophilic character of these new surfactants. The ether junctions between the alkyl chain and carbohydrate moiety proved resistant to severe acid-hydrolytic conditions.