Study of Novel Stilbenyl-Ether-Type Photolabile Protecting Group for a Hydroxyl Group

• Main Authors: Ya-Wen Lee, 李雅雯
• Other Authors: Jinn-Hsuan Ho
• Format: Others
• Language: zh-TW
• Published: 2012
• Online Access: http://ndltd.ncl.edu.tw/handle/s252uz

碩士 === 國立臺灣科技大學 === 化學工程系 === 100 === In this study, we develop a novel stilbenyl-ether-type photolabile protecting group for hydroxyl group in accordance with a acid-catalyzed photochemical rearrangement of 4-methoxystilbene reported by Prof. T.-I. Ho. In the presence of sodium hydride, the alcohol and 1-fluoro-4-styryl-benzene can undergo a one-step protective reaction. We test the stability of these stilbenyl-ether-type compounds in strong reagents. Because of the need of acid-catalysts in this photorelease reaction, we study them in a neutral condition and prove these compounds possess a safe-catch function. We also study the photorelease ability of these compounds under different wavelength irradiations. In addition, we use normal p-methoxystilbenes, styrylarenes, and o-methoxystilbene to study the orthogonal photorelease conditions, including different reaction time and different catalytic conditions. So that a control-release of two alcohols can be achieved. In summary, we successfully developed a novel stilbenyl-ether-type photolabile protecting group.