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

Weizhun Yang; Jicheng Zhang; Chia-Wei Yang; Sherif Ramadan; Richard Staples; Xuefei Huang

doi:10.1021/acs.orglett.0c03394

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

Org Lett. 2021 Feb 19;23(4):1153-1156. doi: 10.1021/acs.orglett.0c03394. Epub 2020 Dec 22.

Authors

Weizhun Yang, Jicheng Zhang, Chia-Wei Yang, Sherif Ramadan¹, Richard Staples, Xuefei Huang

Affiliation

¹ Chemistry Department, Faculty of Science, Benha University, Benha, Qaliobiya 13518, Egypt.

Abstract

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.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Cardiac Glycosides / chemistry*
Cardiac Glycosides / metabolism
Glycosides*
Glycosylation
Molecular Structure

Substances

Cardiac Glycosides
Glycosides

Grants and funding

R01 GM072667/GM/NIGMS NIH HHS/United States