| Summary: | 碩士 === 國立臺灣科技大學 === 化學工程系 === 106 === Deoxy sugar is a core structure dominating an important role in living organisms. However, the mechanism is still unclear because of low yield and poor selectivity in organic synthesis. To achieve these challenges, a one pot synthetic strategy was established by using phenyl thionocarbonyl group. First, with a single step, the phenoxythiocarbonyl donor, a precursor of deoxy sugar, was obtained in high yield. Secondly, phenoxythiocarbonyl donor was employed to achieve stereoselective glycosylation by using neighboring group participation. Finally, the reaction mechanism was clarified in low temperature NMR experiments, and phenyl thionocarbonyl group was applied to control high -selective glycosylation in wide disaccharide molecules.
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