3β,5α,6β-Trihy-droxy-androstan-17-one.

Area of Science:

• Organic Chemistry
• Crystallography
• Computational Chemistry

Background:

• Dehydro-epiandrosterone (DHEA) is a precursor to many steroid hormones.
• Steroid derivatives are of interest for their diverse biological activities.
• Understanding the synthesis and structure of novel steroid compounds is crucial for drug discovery.

Purpose of the Study:

• To synthesize a novel androstan-17-one derivative.
• To elucidate the molecular and crystal structure of the synthesized compound.
• To compare experimental structural data with theoretical calculations.

Main Methods:

• Chemical synthesis involving oxidation and epoxide opening.
• X-ray crystallography for crystal structure determination.
• Quantum mechanical ab initio Roothan Hartree-Fock calculations.

Main Results:

• Successful synthesis of the C(19)H(30)O(4) androstan-17-one derivative.
• Determination of a slightly flattened chair conformation for the six-membered rings and a 14-α envelope conformation for the five-membered ring.
• Observation of a 3D network formed by O-H⋯O hydrogen bonds in the crystal structure.
• Computational calculations closely matched experimental bond lengths, valency angles, and ring torsion angles.

Conclusions:

• The study presents a novel synthetic route to an androstan-17-one derivative.
• The crystal structure reveals specific conformational preferences and intermolecular interactions.
• Theoretical calculations validate the experimental findings, providing insights into the molecule's equilibrium geometry.