Efficient synthesis of a sialic acid alpha(2-->3)galactose building block and its application to the synthesis of ganglioside GM3 |
| |
| Authors: | Liu Yunpeng Ruan Xiaohong Li Xiangpeng Li Yingxia |
| |
| Institution: | Key Laboratory of Marine Drugs, The Ministration of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao, China |
| |
| Abstract: | Glycosylation of various galactose derivatives with O-acetylated sialic acid N-phenyltrifluoroacetimidate as the donor was investigated. Efficient alpha(2,3)sialylation of galactose, with up to 73% yield and 8.4:1 stereoselectivity, was realized when 2,3,4-unprotected galactose derivatives and TBSOTf were used as acceptors and promoter, respectively. Sialylation of 2-(trimethylsilyl)ethyl 6-O-tert-butyldiphenylsilyl-beta-D-galactopyranoside (3f) gave the best result, and the resultant Neu5Ac alpha(2-->3)Gal disaccharide was successfully used in the synthesis of ganglioside GM3. |
| |
| Keywords: | |
| 本文献已被 PubMed 等数据库收录！ |
|
