1.Apply DMF-Modulated Glycosylation to 2,6-dideoxy-a-glycoside synthesis and Extend to the One-Pot Iterative Glycosylation. 2.Development of Remote Picolinoyl-assisted Acceptor Delivery Glycosylation for Deoxy-b-glycoside.

• Main Authors: Ruei, Jyh-Herng, 芮致恆
• Other Authors: Mong, Kwok-Kong Tony
• Format: Others
• Language: zh-TW
• Published: 2014
• Online Access: http://ndltd.ncl.edu.tw/handle/68650171405180195101

碩士 === 國立交通大學 === 應用化學系分子科學碩博士班 === 103 === Deoxysugars play an important role in many antibiotic and pharmaceutical molecules. Therefore, chemical synthesis of 2-deoxy- and 2,6-dideoxyglycoside-containing oligosaccharides are always an interesting topic in carbohydrate field. Our group have found that several additional DMF in glycosylation reaction can significantly increase a selectivity. Recently, we applied this method to different deoxysugars , including 2-deoxygalactose and 2,6-dideoxygalactose. Furthermore, we successfully applied one-pot, iterative, DMF modulated glycosylation to the synthesis of a deoxyglycoside-containing trisaccharides. Protecting groups are also an important factor in glycosylation. Demchenko and co-workers have found that remote O- Picolinoyl group can mediate glycosylation. Picolinoyl may form hydrogen-bond with acceptor and deliver it to the active site from syn side. We applied this concept to the synthesis of 2-deoxy-b-glycosides.