Total Synthesis Of Several 7-Deazapurine Nucleosides

7-Deazapurine nucleoside is a component of natural nucleic acids found in microorganisms and marine organisms that have demonstrated exceptional anti-bacterial, anti-infection, anti-viral, and anti-cancer activity. From synthetic point of view, an efficient methodology for their synthesis is needed urgently,In present dissertation, I focused on solving the challenges that current Vorbruggen glycosylation reaction condition was not suitable for the synthesis of 7-deazapurine nucleoside. The impact of the structure of the nucleoside, the solvent, the temperature, and the nature and the amount of the catalyst was systematically studied and optimized reaction conditions is proposed. Then, the optimized approach was applied successfully for the total synthesis of Toyocamytin, 5’-Deoxytoyocamycin, Cadeguomycin, Mycalisine A and Mycalisine B. It is noteworth to mention that Cadeguomycin and Mycalisine B is the first reported total synthesis. Meanwhile, I also evaluated the microwave equipment to faciliate the Vorbruggen glycosylation reaction. The result showed that microwave heating is very efficient to improve the reaction yield and shorten the reaction time.In summary, the dissertation have developed a general methodology for the syntheis of 7-deazapurine nucleoside. It has the merits of easy handle, high yield and cheap starting material etc. This synthetic approach will have potential impact on development of antitumor drugs based on 7-deazapurine nucleoside.