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

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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.

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Scheme 2

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Acknowledgments

We are grateful to the Deutsche Forschungsgemeinschaft (DFG) for financial support.

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Authors and Affiliations

  1. Department of Biochemical Pharmacy, Institute of Pharmacy, Martin-Luther-University Halle-Wittenberg, Wolfgang-Langenbeck-Str. 4, 06120, Halle (Saale), Germany

    Simon Drescher, Katrin Helmis, Andreas Langner & Bodo Dobner

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  1. Simon Drescher
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  2. Katrin Helmis
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  3. Andreas Langner
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  4. Bodo Dobner
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Correspondence to Simon Drescher.

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Drescher, S., Helmis, K., Langner, A. et al. Synthesis of novel symmetrical, single-chain, diacetylene-modified bolaamphiphiles with different alkyl chain lengths. Monatsh Chem 141, 339–349 (2010). https://doi.org/10.1007/s00706-010-0255-y

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  • DOI: https://doi.org/10.1007/s00706-010-0255-y

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