Studies On The Synthesis Of Glycosyl Indoles Derivatives

Glycosides have long been one of the most popular topics in chemistry and biology, and the abundance of glycosides and indoles in nature and their diverse roles in biological systems make them attractive as subjects for chemical, biological and medicinal research. In this thesis, we start our work for synthesizing glycosyl indoles with aim of combining glycosides with indoles. Our work can be divided some sections as follows.1. The substituted3-hydroxyl indoles were synthesized via different substituted anthranilic acids or2-halogenated benzoic acids via several steps. The structures of the synthesized molecules were characterized by IR,1H NMR or HRMS and the corresponding compounds were hydrolyzed selectively for the work of the second section. And the effects of the ratio among starting materials, reaction time, reaction temperature and other factors were studied. Finally, the optimized synthetic process was established as below:2. The synthetic process of5’-bromo-4’-chloro-3’-hydroindole-2-sialic glycoside was studied and optimized. The products were characterized via IR, HRMS,1H NMR spectra. A lot of work about the factors of reaction temperature, the feasibility of reaction and the availability of reagents was processed, and the better way to prepare the aimed compound was obtained.3. Because of the diverse bioactivities and utility of the a-glycosides in different area, we made our best efforts to synthesize the a-glycosyl indoles with various lewis acids as the catalyst. The work was carried, out as the followed route:...