The Preparation Of 20(S)-Protopanaxadiol And Its Glycosylation With 2-Deoxyglucose

20(S)-protopanaxadiol(PPD)is a very important aglycone in ginsenosides,which has been proved to have a variety of biological activities,especially good anti-tumor activity.It also can be used as a candidate anticancer drug for further research and development.With the research of carbohydrate chemistry becoming a hot spot,the glycosylation structure modification of ginsenosides provides a new way for the drug exploitation of novel ginsenoside derivatives.In order to enhance the anti-cancer activity and druggability of 20(S)-protopanaxadiol,based on the combination principles,this thesis modifies the structure of 20(S)-protopanaxadiol and conducts 2-deoxyglycosidation synthesis research on it,which laid a foundation for the establishment of a synthetic route suitable for industrial production and the further development of new anticancer drug.In this study,total ginsenosides of ginseng root were degraded by acid,the acid degradation process is explored through the orthogonal experiment and the best degradation conditions are determined.The 20(S)-protopanaxadiol was prepared by column chromatography as the raw material for subsequent glycosylation reaction.Then the prepared 20(S)-protopanaxadiol and glycals are protected,added,and deprotected to obtain the 2-deoxyglucoside of 20(S)-protopanaxadiol.The structure of each product acquired in the reaction was identified by nuclear magnetic resonance spectroscopy(NMR).During the experiment,the single factor experiment was carried out on the reaction temperature,reaction time,feed ratio and catalyst,then the orthogonal test method was used to study for further screen and verify the reaction conditions.Finally,the best synthetic method for the 2-deoxyglycosylation derivative of 20(S)-protopanaxadiol was determined.The proposed approach has following benefits,the material required is easy to obtain,the method is simple and fast,and is more conducive to the expansion of the production of drugs compared with the previous synthetic methods.It provides a reference for the 2-deoxyglycosylation of ginsenoside by deoxy sugar and the development of new potential anti-cancer drugs of ginsenoside.