engleski

Design of a depside with a lipophilic adamantane moiety : Synthesis, crystal structure and molecular conformation

New adamantane depsides, ethyl 2-(1-adamantyl)-3-O-[(S)-Boc-Phe]butanoate (R, R, S)-1a and (S, S, S)-1b were prepared and characterized by spectroscopic data. The crystal structures and the stereochemistry of rac-(R, R, S)-1a and threo-2-(1-adamantyl)-3-hydroxy-butanoic acid rac-(R, R)-4a were determined by X-ray structure analysis. In the racemic crystal, the molecules of 1a from centrosymmetric dimers through hydrogen bonds involving a double acceptor function of the depside carbonil oxygen, and donors of the amino group and aromatic C-H atoms. The dimers are connected through an infinite chain of C-H...O interactions, were C-H is an aromatic donor and the ester carbonil oxygen is an acceptor. In the solid state, amphilic molecules 1a and 4a exihibit pronouced hydrophilic and hydropfobic biliayers.

depside design; adamantyl hydroxybutanoic acid; conformation; X-ray structure analysis

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