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

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@article{1b2f7a0eabf24a25a8317f2d778d164f,

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",

issn = "1523-7060",

publisher = "American Chemical Society",

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}

TY - JOUR

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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U2 - 10.1021/acs.orglett.9b03321

DO - 10.1021/acs.orglett.9b03321

M3 - Article

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VL - 21

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JO - Organic letters

JF - Organic letters

SN - 1523-7060

IS - 21

ER -

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

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