Synthesis, NMR and crystal characterization of dimeric terephthalates derived from epimeric 4,5-seco-cholest-3-yn-5-ols

• Both epimeric of 4,5-secocholest-3-yn-5-ols were prepared from cholesterol.
• Reaction with terephthaloyl chloride led to crystalline dimeric terephthalates.
• The configuration at C-5 plays an important role in the crystal packing.
• Hydrophobic interactions promote multilayer or helicoidal self assemblies.

Two dimeric steroidal terephthalates derived from epimeric 4,5-seco-cholest-3-yn-5-ols were prepared starting from cholesterol in a five-step synthetic sequence. X-ray crystallography shows that the obtained compounds display novel supramolecular networks in the solid state in which the facial hydrophobicity of the steroidal skeletons plays an important role. Unambiguous NMR characterization of the obtained dimers is also provided.

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