Long-Range Stereodirecting Participation across a Glycosidic Linkage in Glycosylation Reactions

被引:10
|
作者
Yang, Weizhun [1 ]
Zhang, Jicheng [1 ]
Yang, Chia-Wei [1 ]
Ramadan, Sherif [1 ,2 ]
Staples, Richard [1 ]
Huang, Xuefei [3 ,4 ]
机构
[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
[2] Benha Univ, Fac Sci, Chem Dept, Banha 13518, Qaliobiya, Egypt
[3] Michigan State Univ, Dept Chem, Inst Quantitat Hlth Sci & Engn, E Lansing, MI 48824 USA
[4] Michigan State Univ, Dept Biomed Engn, E Lansing, MI 48824 USA
基金
美国国家科学基金会;
关键词
NEIGHBORING GROUP PARTICIPATION; CHEMICAL-SYNTHESIS; SULFATE; PERSPECTIVES; STRATEGY; ACIDS;
D O I
10.1021/acs.orglett.0c03394
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The formation of an unprecedented 12-membered macrocyclic ketal through the long-range participation of a levulinoyl group across a glycosidic linkage was observed in glycosylation reactions. This finding indicated that stereodirecting participation is not limited to groups within the glycan ring being activated, thus broadening the scope of remote group participation in glycosylation.
引用
收藏
页码:1153 / 1156
页数:4
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