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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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N-tert-Butyl-3-hydr-oxy-5-androstene-17-carboxamide monohydrate.

Jiang-Sheng Li, Jim Simpson, Xiao-Jun Li

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary

    This study details the crystal structure of a pregnenolone derivative, revealing specific molecular conformations and hydrogen bonding patterns. The bulky tert-butyl group prevents N-H hydrogen bonding, influencing crystal packing.

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Structural Biology

    Background:

    • Steroids are a crucial class of organic compounds with diverse biological functions.
    • Understanding the precise three-dimensional structure of steroid derivatives is essential for elucidating their activity.
    • Pregnenolone derivatives are key intermediates in steroid biosynthesis.

    Purpose of the Study:

    • To determine the crystal structure of a specific pregnenolone derivative, C(24)H(39)NO(2)·H(2)O.
    • To analyze the conformational details of the steroid rings and substituents.
    • To investigate the intermolecular interactions, including hydrogen bonding, within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to obtain the structural data.
    • Analysis of bond lengths, bond angles, and torsion angles elucidated the molecular geometry.
    • Identification of hydrogen bonds and packing arrangements was performed.

    Main Results:

    • The A and C rings adopted chair conformations, while the B ring was a flattened chair, and the D ring exhibited an envelope conformation.
    • The N-tert-butyl-carboxamide group was found in an equatorial position.
    • Disordered hydrogen atoms were observed for the 3β-hydroxyl group and the water molecule.
    • Hydrogen bonding formed dimers via the 3β-hydroxyl groups, further stacked by water molecules.
    • The N-tert-butyl group sterically hindered N-H hydrogen bond formation.

    Conclusions:

    • The crystal structure provides detailed insights into the conformational preferences of this pregnenolone derivative.
    • Intermolecular hydrogen bonding, mediated by hydroxyl and water groups, dictates the crystal packing.
    • The steric bulk of the tert-butyl substituent significantly impacts the hydrogen bonding network.