請用此 Handle URI 來引用此文件: http://hdl.handle.net/11455/90579
標題: Total Synthesis of Ganglioside Hp-s1
醣苷神經鞘胺脂質 Hp-s1之全合成
作者: 陳宛欣
Wan-Shin Chen
關鍵字: ganglioside Hp-s1 1
neuritogenic activity
stereoselectivity
醣苷神經鞘胺脂質
神經再生活性
立體位向選擇
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摘要: Total synthesis of the ganglioside Hp-s1 1, which was identified from the ovary of sea urchin Diadema setosum and displays neuritogenic activity is described. The characteristic sequence of the disaccharide part was efficiently assembled by coupling of a highly active benzyl protected glucosyl donor and a phytosphingosine derived acceptor with high stereoselectivity, leaving the primary hydroxyl group of the glucoside acceptor free for further glycosylation. The corresponding disaccharyl acceptor was directly glycosidated with the acetyl-protected sialyl donor part to afford the trisaccharide in high yield and stereoselectivity. After amidization formation and global deprotection, ganglioside Hp-s1 1 was obtained.
利用化學方法合成出Hp-s1 1。Hp-s1 1可由刺冠海膽的卵巢中所分離得到,為一種具神經再生活性的醣苷神經鞘胺脂質。在第一部分的醣鏈結反應中,以具有高反應性苄基保護基的葡萄醣醣予體與植物神經鞘胺醇醣受體進行反應,可獲得良好的立體位向選擇,再以此雙醣化合物與唾液酸醣予體進行醣鏈結反應,也可得到高產率之三醣產物,且也具有良好之立體位向選擇。後續經由醯胺化反應及去保護基反應,可成功合成目標物Hp-s1 1。
URI: http://hdl.handle.net/11455/90579
文章公開時間: 2016-01-28
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