| Summary: | 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.
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