A synthetic strategy for novel nonsymmetrical bola amphiphiles based on carbohydrates.
A number of novel nonionic bolaform amphiphiles with nonidentical aldityl head groups, 1-(1-deoxy-D-galactitol-1-ylamino)-6-(1-deoxy-D-glucitol-1-ylamino)hexane, 1-(1-deoxy-D-mannitol-1-ylamino)-6-(1-deoxy-D-glucitol-1-ylamino)hexane, and 1-(1-deoxy-D-galactitol-1-ylamino)-6-(1-deoxy-D-mannitol-1-ylamino)hexane were synthesized by two successive reductive aminations involving 1,6-diaminohexane (1) and the appropriate D-aldohexoses (D-glucose, D-mannose, and D-galactose) using 5% Pd on carbon as the catalyst. Typical reaction conditions were 40 degrees C, 4MPa hydrogen and a reaction time of 4.5 h. The compounds were isolated as white solids in yields ranging from 39% to 72%. The intermediate aminoalditols, 1-(1-deoxy-D-glucitol-1-ylamino)-6-aminohexane and 1-(1-deoxy-D-galactitol-1-ylamino)-6-aminohexane were obtained as off-white solids in 80-85% yield. The bolaform amphiphiles containing 1-deoxy-D-glucitol head group(s) showed markedly lower melting points than the compounds with the 1-deoxy-D-mannitol and 1-deoxy-D-galactitol head groups, due to the presence of 1,3-syn interactions within the carbohydrate moiety. The novel bolaform compounds are potential starting materials for the synthesis of a broad range of gemini surfactants with nonidentical, carbohydrate-based head groups.
Schuur
Boelo
B
Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Wagenaar
Anno
A
Heeres
André
A
Heeres
Erik H J
EH
D001671:Biochemistry / Q000379:methods*; D002241:Carbohydrates / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D010455:Peptides / Q000138:chemical synthesis*; D013501:Surface-Active Agents / Q000737:chemistry; D013997:Time Factors
D002241:Carbohydrates; D007202:Indicators and Reagents; D010455:Peptides; D013501:Surface-Active Agents; D002244:Carbon; D006859:Hydrogen