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

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