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

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2019
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Liu, Hui
Hansen, Thomas
Zhou, Si-Yu
Wen, Guo-En
Liu, Xu-Xue
Zhang, Qing-Ju
Codée, Jeroen D. C.
Sun, Jian-Song
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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.

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ISO 690LIU, Hui, Thomas HANSEN, Si-Yu ZHOU, Guo-En WEN, Xu-Xue LIU, Qing-Ju ZHANG, Jeroen D. C. CODÉE, Richard R. SCHMIDT, Jian-Song SUN, 2019. Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions. In: Organic Letters. 2019, 21(21), pp. 8713-8717. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.9b03321
BibTex
@article{Liu2019-11-01DualP-47666,
  year={2019},
  doi={10.1021/acs.orglett.9b03321},
  title={Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions},
  number={21},
  volume={21},
  issn={1523-7060},
  journal={Organic Letters},
  pages={8713--8717},
  author={Liu, Hui and Hansen, Thomas and Zhou, Si-Yu and Wen, Guo-En and Liu, Xu-Xue and Zhang, Qing-Ju and Codée, Jeroen D. C. and Schmidt, Richard R. and Sun, Jian-Song}
}
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