Polar corticosteroids in human neonatal urine; synthesis and gas chromatography-mass spectrometry of ring A reduced 6-hydroxylated corticosteroids

Abstract

This report describes the synthesis of 3alpha,6beta,11beta,17alpha,21-pentahydroxy-5beta-pregnane-20-one, 3alpha,6beta,11beta,17alpha,21-pentahydroxy-5beta-pregnane-20-one, 3alpha,6alpha,11beta,17alpha,21-pentahydroxy-5alpha-pregnane-20-one, 3alpha,6beta,17alpha,21-tetrahydroxy-5beta-pregnane-11,20-dione, 3alpha,6beta,17alpha,21-tetrahydroxy-5alpha-pregnane-11,20-dione, 3alpha,6alpha,17alpha,21-tetrahydroxy-5beta-pregnane-11,20-dione and 3alpha,6alpha,17alpha,21-tetrahydroxy-5alpha-pregnane-11,20-dione. The gas chromatographic-mass spectrometric properties of these compounds are given. Proof of structure was accomplished using gas chromatography-mass spectrometry, microchemical reactions, optical rotatory dispersion and nuclear magnetic resonance spectroscopy.