Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions

Hui Liu, Thomas Hansen, Si Yu Zhou, Guo En Wen, Xu Xue Liu, Qing Ju Zhang, Jeroen D.C. Codeé*, Richard R. Schmidt, Jian Song Sun*

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

The 2,2-dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) group permits, via robust neighboring group participation (NGP) or long distance participation (LDP) effects, the stereocontrolled 1,2-trans, 1,2-cis, as well as β-2,6-dideoxy glycosidic bond generation, while suppressing the undesired orthoester byproduct formation. The robust stereocontrol capability of the DMNPA is due to the dual-participation effect from both the ester functionality and the nitro group, verified by control reactions and DFT calculations and further corroborated by X-ray spectroscopy.

Original languageEnglish
Pages (from-to)8713-8717
Number of pages5
JournalOrganic letters
Volume21
Issue number21
DOIs
Publication statusPublished - 1 Nov 2019

Funding

This work was financially supported by the National Natural Science Foundation of China (21572081, 21762024, and 21877055) and Natural Science Foundation of Jiangxi Province (20161ACB20005, 20171BCB23036, and 20171BAB203008). The Innovative Fund of Jiangxi Province to H.L. (YC2018-B031) was also appreciated. The authors thank the SURFsara for use of the Lisa.

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