1028796-03-3Relevant academic research and scientific papers
Efficient synthesis of a sialic acid α(2→3)galactose building block and its application to the synthesis of ganglioside GM3
Liu, Yunpeng,Ruan, Xiaohong,Li, Xiangpeng,Li, Yingxia
, p. 4287 - 4290 (2008)
(Chemical Equation Presented) Glycosylation of various galactose derivatives with O-acetylated sialic acid N-phenyltrifluoroacetimidate as the donor was investigated. Efficient α(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-β-D-galactopyranoside (3f) gave the best result, and the resultant Neu5Ac α(2→3)Gal disaccharide was successfully used in the synthesis of ganglioside GM3.
