Vargas-Romero, K., Martínez-Torres, F.C., Aguilar-Granda, A., Pérez-Estrada, S., Flores-Alamo, M., Rodríguez-Molina, B., Iglesias-Arteaga, M.A. Synthesis and Solid-State Dynamics of a Crystalline Steroid Molecular Rotor without the Alkyne Axle: Steroid Dimers Based on a 1,4-Di(1,3-dioxan-2-yl)benzene. Journal of Organic Chemistry. 2020, 85, 8501-8509. DOI: 10.1021/acs.joc.0c00867
Two diastereomeric crystalline steroid dimers were obtained by acid-catalyzed double acetalization of (20S)-5?-pregnan-3?,16?,20-triol 3-monoacetate with terephtalaldehyde. These compounds were characterized by NMR in solution, MS, single-crystal X-ray diffraction, and variable-temperature solid-state NMR by 13C cross-polarization magic angle spinning (CPMAS). While the phenylene rotator in the SR diastereomer remains static even at 373 K, the RR isomer shows a slow rotational process of the phenylene ring at temperatures above room temperature and thus may be considered the first crystalline steroid molecular rotor without the alkyne axle.