Open AccessLong-Range Stereodirecting Participation across a Glycosidic Linkage in Glycosylation Reactions
Author(s) -
Weizhun Yang,
Jicheng Zhang,
ChengTa Yang,
Sherif Ramadan,
Richard J. Staples,
Xuefei Huang
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c03394
Subject(s) - glycosidic bond , chemistry , glycosylation , glycan , scope (computer science) , ring (chemistry) , group (periodic table) , stereochemistry , linkage (software) , glycoprotein , organic chemistry , biochemistry , gene , programming language , computer science , enzyme
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.