Synthesis of a number of novel pregnane derivatives has been described in detail. They were prepared by reaction of 3b-hydroxy-5, 16-pregnadiene-20-one (2) with diethylene glycol, 2-methoxy ethanol, 1,2-propane diol, p-chloroaniline and p-fluoroaniline, respectively. The structures of these newly synthesized compounds have been established on basis of physical, analytical and spectral data. These pregnane derivatives have been evaluated for their anti-dyslipidemic activity (Triton model) and in vitro antioxidant activities. Out of the 12 compounds tested, 3 of them showed potent anti-dyslipidemic activity and 7 showed potent antioxidant and scavenger of oxygen free radicals.