Synthetic Studies of Pseudouridine via Palladium-catalyzed Heck-type Glycosylation Reaction

• Main Authors: Chang, Hsin-Yun, 張馨云
• Other Authors: Chien, Tun-Cheng
• Format: Others
• Language: zh-TW
• Published: 2016
• Online Access: http://ndltd.ncl.edu.tw/handle/58799143635724803610

碩士 === 國立臺灣師範大學 === 化學系 === 104 === The nucleosidic bond of C-nucleosides are much more stable than N-nucleosides, which allows potential applications of C-nucleosides in medi-cinal chemistry and chemical biology. Some of the naturally occurring C-nucleosides possess a wide variety of biological activities. We are particu-larly interested in the synthesis of pseudouridine and 2’-deoxypseudouridine. In this thesis, we employed Heck-type coupling reactions to form C-C bonds between the anomeric carbon of 1, 2-unhydrous sugar derivatives and aryl iodides or iodo-heterocycles. Instead of utilizing toxic and expensive AsPh3 as the ligand, tour study has showed that the use of bidentate ligands for Heck-type coupling reactions were highly regio- and stereoselective. The methodology is applicable to the synthesis of 2’-deoxypseudouridine and pseudouridine.