Studies On Synthesis Of 7-Ketocholesterol And 7β-Hydroxycholesterol

7-Ketocholesterol and 7/β-Hydroxycholesterol are extracted from Oviductus Ranae of the first time, and they belong to the sterols. However, owing to the complex methods, long time consuming, low yield, high cost and the low content of 7-Ketocholesterol and 7β-Hydroxycholesterol in which is expensive, it is unavailable to aqcuire 7-Ketocholesterol and 7β-Hydroxycholesterol just by the extraction from Oviductus Ranae. In order to demonstrate the activities of 7-Ketocholesterol and 7β-Hydroxycholesterol and develop them, as well as to widen the field of studies on the effective constituents and identification of the authenticity of Oviductus Ranae, to promote the development of Chinese medicine, we can acquire the target compound by chemical synthesized method.Sterols are widely in body tissues which play an important role of the biological life. Dr.Weitzman who has called it "the key of life" reveals the importance of such substances. Currently, sterols are widely used in medicine, food, chemical feed, plant genetic engineering and science research and other fields. With the rapid development of science and technology, studies on sterols have the broad prospects.In this experiment, in order to the protect C-3 hydroxyl of Cholesterol that we changed Cholesterol to Cholesteryl Acetate. Synthesis of Cholesteryl Acetate was by Acetic Anhydride. Identification of chemical structure of it was by determination of melting point,1H-NMR and IR, and this compound is Cholesteryl Acetate. Through single factor test we chosed reaction temperature, reaction time, volume of acetic anhydride and volume of pyridine of the four factors for degradation process researching. The results showed that the optimal conditions for degradation was under 75℃,20ml acetic anhydride and 15ml pyridine react 6h. Finally, the synthesis technology of validate test of results show that the method is stable, viable, and high yield.Synthesis of intermediate 7-Ketocholesterol Acetate is that Cholesteryl Acetate has been added one Carbonyl on the C-7. Because the C-5 double bond could not be damaged in the reaction, we choose the selective oxidation function of allylic oxidant.Identification of Chemical Structure of it was by determination of melting point,1H-NMR and IR, and this compound is 7-Ketocholesterol Acetate. In addition, we wanted to select a synthesis method which were cheaper, security, to protect environment and high yield with few by-products, we selection five representative allylic oxidant which had the high yield in the literature to compare which one is the best. These allylic oxidants are Collins, PCC-SiO2, THBP-CrO3, TBHP-CuCl2-Bu4NBr and Air-NHPI.. Finally, we selected THBP-CrO3 oxidation system as the optimal method. The method was with high yield, relatively few impurities, simple operation, low cost, to get easily and less consumption, safety and to protect environment, efficient. Finally, the synthesis technology of validate test of results show that the method is stable, viable, and high yield.7-Ketocholesterol came from 7-Ketocholesterol Acetate by alkaline hydrolysis. This method was with high yield and simple operation. Identification of chemical structure of it was by determination of 13C-NMR,'H-NMR and DEPT, and this compound is 7-Ketocholesterol.Preparation of 7β-Hydroxycholesterol is the C-7 carbonyl group of 7-Ketocholesterol Acetate reduces toβconfiguration hydroxyl group, then to get target compound by alkaline hydrolysis. We use NaBH4/CeCl3 to get theβconfiguration of the target product. Dentification of chemical structure of it was by determination of 13C-NMR,1H-NMR and DEPT, and this compound is 7β-Hydroxycholesterol.