Glycosyl Chloride-mediated Stereoselective Glycosylation Reaction of 2-Deoxy galactose

• Main Authors: Yi-Pei Liu, 劉宜佩
• Other Authors: Cheng-Chung Wang
• Format: Others
• Language: zh-TW
• Published: 2014
• Online Access: http://ndltd.ncl.edu.tw/handle/59381248131476647794

碩士 === 國立中央大學 === 化學學系 === 102 === Sugars are widely distributed in nature, and play important roles in living systems. Controlling the stereoselectivity in glycosylation reactions is a challenging issue in carbohydrate chemistry. Different from commonly believed in the literature, we have found that the chloride from the promoters actually participates into the glycosylation reactions, and the chloride- intermediates affects the stereoselectivity. From ours discovery, we understand the importance of the glycosyl-chloride intermediate. In this thesis, we focus on how the influence of 2-deoxygalactosyl chloride intermediates affects the stereoselectivity of their glycosylation reactions. We first identified the 2-deoxygalactosyl intermediates by NMR spectroscopy under low temperature. Furthermore, we added different types of promoters and additives in the reaction to investigate their effect to the stereoselectivity of the glycosylation reactions.