Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions
| Type of Publication: | Journal article |
| Publication status: | Published |
| Author: | Liu, Hui; Hansen, Thomas; Zhou, Si-Yu; Wen, Guo-En; Liu, Xu-Xue; Zhang, Qing-Ju; Codée, Jeroen D. C.; Schmidt, Richard R.; Sun, Jian-Song |
| Year of publication: | 2019 |
| Published in: | Organic Letters ; 21 (2019), 21. - pp. 8713-8717. - ISSN 1523-7060. - eISSN 1523-7052 |
| Pubmed ID: | 31613104 |
| DOI (citable link): | https://dx.doi.org/10.1021/acs.orglett.9b03321 |
| Summary: |
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.
|
| Subject (DDC): | 540 Chemistry |
| Bibliography of Konstanz: | Yes |
| Refereed: | Yes |
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LIU, 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. 21(21), pp. 8713-8717. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.9b03321
@article{Liu2019-11-01DualP-47666, title={Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions}, year={2019}, doi={10.1021/acs.orglett.9b03321}, 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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