Synthesis of Novel Asymmetrical Single-Chain Phosphoglycol-Based Bolaamphiphiles

Abstract

The synthesis of long-chain 1,ω-diols with orthogonal cleavable protecting groups can be effectively performed with the use of the Grignard coupling reaction, successfully leading to the preparation of novel asymmetrical single-chain phosphoglycol-based bolaamphiphiles—a side-product that always occurred during the synthesis of symmetrical bolalipids.

[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]

GRAPHICAL ABSTRACT

Keywords:

• Bipolar lipids
• bolaamphiphiles
• Grignard reaction
• synthetic methods

ACKNOWLEDGMENTS

We thank Andrea Sinz and Christian Ihling (Department of Pharmaceutical Chemistry and Bioanalytics, Martin-Luther-University, Halle-Wittenberg) for the high-resolution mass spectrometry analysis.