从海洋海绵Agela clathrodes中分离出的一种新型糖鞘脂类化合物克拉哈莫糖苷的简洁合成。

Concise synthesis of clarhamnoside, a novel glycosphingolipid isolated from the marine sponge Agela clathrodes.

作者信息

Ding Ning, Li Chunxia, Liu Yunpeng, Zhang Zaihong, Li Yingxia

机构信息

Key Laboratory of Marine Drugs, The Ministration of Education of China, School of Pharmacy, Ocean University of China, Qingdao 266003, China.

出版信息

Carbohydr Res. 2007 Oct 15;342(14):2003-13. doi: 10.1016/j.carres.2007.05.018. Epub 2007 May 18.

DOI:10.1016/j.carres.2007.05.018

PMID:17559820

Abstract

The first total synthesis of a novel alpha-galactoglycosphingolipid clarhamnoside has been achieved through a straightforward strategy. A thiogalactosyl donor with a benzylidene group at C-4 and C-6 and nonparticipating p-methoxybenzyl group at C-2 was successfully employed in the stereocontrolled syntheses of alpha-GalGSLs. The N-Phth-protected trifluoroacetimidate donor for terminal disaccharide was successfully applied in constructing the [GalNAc beta-(1-->6)-Gal] glycosidic linkage.

摘要

通过一种直接的策略首次实现了新型α-半乳糖糖鞘脂克拉哈糖苷的全合成。一种在C-4和C-6位带有亚苄基且在C-2位带有非参与性对甲氧基苄基的硫代半乳糖基供体成功地用于α-半乳糖糖鞘脂的立体控制合成。用于末端二糖的N-邻苯二甲酰保护的三氟乙酰亚氨酸酯供体成功地应用于构建[GalNAcβ-(1→6)-Gal]糖苷键。