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

Hui Liu | Zendy; Thomas Hansen | Zendy; Si-Yu Zhou | Zendy; Guo-En Wen | Zendy; Xu-Xue Liu | Zendy; Qing-Ju Zhang | Zendy; Jeroen D. C. Codée | Zendy; Richard R. Schmidt | Zendy; Jiansong Sun | Zendy

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

Author(s) -

Hui Liu,

Thomas Hansen,

Si-Yu Zhou,

Guo-En Wen,

Xu-Xue Liu,

Qing-Ju Zhang,

Jeroen D. C. Codée,

Richard R. Schmidt,

Jiansong Sun

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b03321

Subject(s) - chemistry , orthoester , glycosidic bond , anomer , protecting group , group (periodic table) , anomeric effect , glycosylation , nitro , stereochemistry , dual (grammatical number) , combinatorial chemistry , organic chemistry , enzyme , biochemistry , art , alkyl , literature

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- rans , 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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