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The synthesis of six 2O-deoxy steroids derived from 3a-hydroxy-5p-pregnane is described. These compounds, three of which are new, were interrelated by a number of reactions. The 20-deoxy steroids and their derived acetates were used as compounds of reference in an extended study centering on the absolute contribution to optical rotatory activity of C-20 epimeric hydroxyl and acetoxyl groups. The influence of a variety of substituents at C-17 and C-21 on the qualitative and quantitative shifts in molecular rotation brought about by oxygen functions at C-20 is discussed.