Monatshefte für Chemie - Chemical Monthly

, Volume 141, Issue 3, pp 339–349 | Cite as

Synthesis of novel symmetrical, single-chain, diacetylene-modified bolaamphiphiles with different alkyl chain lengths

  • Simon Drescher
  • Katrin Helmis
  • Andreas Langner
  • Bodo Dobner
Original Paper

Abstract

General syntheses of novel symmetrical, single-chain, diacetylene-modified bolaphospholipids have been carried out in five steps. For the ω-alkynols, which have an important role as key intermediates, three different synthetic approaches were comprehensively investigated. For the final synthesis it is suggested that (1) alkylation of lithium (trimethylsilyl)acetylide with tetrahydropyranyl-protected ω-bromoalcohols, followed by (2) cleavage of the trimethylsilyl moiety and the tetrahydropyranyl protecting group, and (3) copper(II)-catalyzed Eglinton coupling is the best strategy for obtaining diacetylene-modified alkane-1,ω-diols, because higher yields were obtained while avoiding the formation of by-products. Moreover, conversion of the diols into bipolar phospholipids was achieved by bis-phosphorylation with β-bromoethylphosphoric acid dichloride and subsequent quaternization with trimethylamine or dimethylamine. Finally, spectral data are presented for novel single-chain, diacetylene-modified bolaphospholipids with promising potential as starting molecules in the formation of polymerizable and, thus, thermostable nanofibers.

Graphical abstract

Keywords

Alkynes Diacetylenes Lipids Nanostructures Phosphates Phospholipids 

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Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  • Simon Drescher
    • 1
  • Katrin Helmis
    • 1
  • Andreas Langner
    • 1
  • Bodo Dobner
    • 1
  1. 1.Department of Biochemical Pharmacy, Institute of PharmacyMartin-Luther-University Halle-WittenbergHalle (Saale)Germany

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