Phosphite-assisted and Michael Addition of Endo- glycal

• Main Authors: Su-I Wang, 王思懿
• Other Authors: 林煇章
• Format: Others
• Language: zh-TW
• Published: 2011
• Online Access: http://ndltd.ncl.edu.tw/handle/68888043677664143738

碩士 === 中國醫藥大學 === 藥物化學研究所碩士班 === 99 === 2,3-unsaturated glycosides were successfully synthesized by means of allylic phosphite-assisted glycosylation. Endo-Glycosyl phosphite were treated with catalytic amount of AlCl3 and various O-nucleophiles including alcohols and sugars under the mild conditions. The desired α-O-glycosides products were obtained in good to excellent yields with high stereoselectivity(α/β?d92/8) . This paper also describes a new synthetic route towards 6-amino hex-1-en-3-uloses and azepane derivatives starting from 3,4,6-tri-O-acetyl-D-glucal. The method involves allylic alcohol was oxidated and azide group was reducted to afford the 6-amino hex-1-en-3-uloses. However, we can not afforded the azepane derivatives by Intramolecular Michael addition of 6-amino hex-1-en-3-uloses.