糖基化
化学
立体选择性
位阻效应
立体化学
糖基供体
糖基
会聚合成
低聚糖
有机化学
生物化学
催化作用
作者
Qingpeng Zhao,Shihao Zhou,Yue Wang,Xiaoyu Yang,Youhui Meng,Yanxin Zhang,Jian Gao
标识
DOI:10.1016/j.cclet.2022.107982
摘要
A family of the 3,6-branched Fuzi α-glucans including the pentasaccharide repeating unit as well as its di- and trimers were efficiently achieved via a one-pot and convergent glycosylation strategy. All the protected α-glucans up to 15-mer were assembled with high yields and excellent α-stereoselectivity, which was secured by the synergistic α-directing effects of the TolSCl/AgOTf promotion system and the steric β-facial shielding of bulky saccharide residues linked at the 6-O-position of glucosyl donors. Moreover, the 3,6-branched architecture of glycosyl donor was revealed to be more favorable for the α-selective glucosidation of primary hydroxyl group, especially in the case of large oligosaccharide acceptor. The structurally well-defined synthetic α-glucans would be useful for various biological studies.
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