A synthetic strategy for novel nonsymmetrical bola amphiphiles based on carbohydrates

Boelo Schuur, Anno Wagenaar, André Heeres, Erik H.J. Heeres*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

14 Citations (Scopus)

Abstract

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 (4a), 1-(1-deoxy-D-mannitol-1-ylamino)-6-(1-deoxy-D-glucitol-1-ylamino) hexane (4b), and 1-(1-deoxy-D-galactitol-1-ylamino)-6-(1-deoxy-D-mannitol-1- ylamino)hexane (4c) 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°C, 4MPa hydrogen and a reaction time of 4.5h. 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 (3a) and 1-(1-deoxy-D-galactitol-1-ylamino)-6-aminohexane (3b) 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.

Original languageEnglish
Pages (from-to)1147-1153
Number of pages7
JournalCarbohydrate Research
Volume339
Issue number6
DOIs
Publication statusPublished - 28 Apr 2004
Externally publishedYes

Keywords

  • Carbohydrates
  • Nonionic bolaform amphiphiles
  • Reductive amination

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