title: A steroid structure which refutes the isolation of C(17)-C(20) rotational isomers.
abstract: Isolation of two C(17)-C(20) rotamers of 20-methyl-20-(2-hydroxyethoxy)-5-pregnene-3beta, 17alpha-diol has been reported. X-Ray analysis of a diacetate derivative of one of the "rotamers" shows that the actual structure is 3beta-acetoxy-17aalpha-(2-acetoxyethoxy)-17alpha,17abeta-dimethyl-D-homo-5-androsten-17beta-ol (C28H44O6). Thus, although this investigation refutes the existence of C(17)-C(20) rotamers, it suggests a possible new pathway for D-homo steroid synthesis.
mesh_terms: D006718:Homosteroids; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D011283:Pregnenes; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D014961:X-Ray Diffraction
chemical_list: D006718:Homosteroids; D011283:Pregnenes