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

doi:10.1021/acs.orglett.9b03321

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

Chemistry and Pharmaceutical Sciences

Research output: Contribution to Journal › Article › Academic › peer-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 language	English
Pages (from-to)	8713-8717
Number of pages	5
Journal	Organic letters
Volume	21
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.9b03321
Publication status	Published - 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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10.1021/acs.orglett.9b03321

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title = "Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions",

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.",

author = "Hui Liu and Thomas Hansen and Zhou, {Si Yu} and Wen, {Guo En} and Liu, {Xu Xue} and Zhang, {Qing Ju} and Code{\'e}, {Jeroen D.C.} and Schmidt, {Richard R.} and Sun, {Jian Song}",

year = "2019",

month = nov,

day = "1",

doi = "10.1021/acs.orglett.9b03321",

language = "English",

volume = "21",

pages = "8713--8717",

journal = "Organic letters",

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T1 - Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions

AU - Liu, Hui

AU - Hansen, Thomas

AU - Zhou, Si Yu

AU - Wen, Guo En

AU - Liu, Xu Xue

AU - Zhang, Qing Ju

AU - Codeé, Jeroen D.C.

AU - Schmidt, Richard R.

AU - Sun, Jian Song

PY - 2019/11/1

Y1 - 2019/11/1

N2 - 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.

AB - 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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JO - Organic letters

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

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