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 Moiety
journal contributionposted on 12.06.2020, 21:13 by Katherine Vargas-Romero, Fátima C. Martínez-Torres, Andrés Aguilar-Granda, Salvador Pérez-Estrada, Marcos Flores-Alamo, Braulio Rodríguez-Molina, Martín A. Iglesias-Arteaga
Two diastereomeric crystalline steroid dimers were obtained by acid-catalyzed double acetalization of (20S)-5α-pregnan-3β,16β,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.
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Alkyne AxlesolutionRR isomerSolid-State DynamicsmonoacetatediastereomericMSphenylene rotatoracid-catalyzed373 K13 C cross-polarization magic angleSteroid DimersSynthesidimersrotorSR diastereomerterephtalaldehydecompoundalkyne axleNMRvariable-temperaturephenylene ringCrystalline Steroid Molecular RotorCPMASroom temperature3-acetalizationMoietysingle-crystal X-ray diffraction