Assembly of Digitoxin by Gold(I)-Catalyzed Glycosidation of Glycosyl o-Alkynylbenzoates
Assembly of Digitoxin by Gold(I)-Catalyzed Glycosidation of Glycosyl o-Alkynylbenzoates
复制标题
金(I)催化糖基邻炔基苯甲酸酯糖苷化组装洋地黄毒苷
DOI：
10.1021/jo201850z
复制
发表时间：
2011-12-02
影响因子：
3.6
通讯作者：
Yu, Biao
中科院分区：
文献类型：
--
作者：
Ma, Yuyong;Li, Zhongzhen;Yu, Biao
洋地黄毒苷是一种临床上重要的心脏三囊体，由洋地黄毒苷配基和3，4-二-O-叔丁基二苯基甲硅烷基-D-洋地黄毒苷基-O-环丙基乙炔基-苯甲酸酯通过交替糖基化和保护基操作，经9步有效地合成，总收率为52%。本合成展示了金（I）催化的糖基化方案在合成含有酸不稳定的2-脱氧糖键的糖缀合物中的优势。
Digitoxin, a clinically important cardiac trisactharicle, was assembled efficiently from digitoxigenin and 3,4-di-O-tert-butyldiphenylsilyl-D-digitoxosyl o-cyclopropylethynyl-benzoate in 9 steps and 52% overall yield via alternate glycosylation and protecting group manipulation. The present synthesis showcases the advantage of the gold(I)-catalyzed glycosylation protocol in the synthesis of glycoconjugates containing acid-labile 2-deoxysugar linkages.