Dual Anomeric Stereocontrol in 1,1′-Glycosylation via a Remote Directing 2-(Diphenylphosphinoyl)acetyl Group

The stereoselective construction of 1,1'-glycosidic linkages represents a significant challenge, as it typically results in a mixture of four possible anomers. Herein, we report a novel and efficient method to achieve this transformation leveraging a remote directing 2-(diphenylphosphinoyl)acetyl (DPPA) group on donors for catalytic glycosylation. This approach provides exceptional dual anomeric stereocontrol for both glycosyl donors and acceptors, which we attribute to the DPPA's role as a powerful hydrogen-bonding (H-bonding) acceptor.

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Publication Details

Journal
Organic Letters
Published
2025-12-03
DOI
https://doi.org/10.1021/acs.orglett.5c04451
Citations
1
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
Field-Weighted Citation Impact
0.94
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article

Dual Anomeric Stereocontrol in 1,1′-Glycosylation via a Remote Directing 2-(Diphenylphosphinoyl)acetyl Group

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1 citations
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article

Dual Anomeric Stereocontrol in 1,1′-Glycosylation via a Remote Directing 2-(Diphenylphosphinoyl)acetyl Group

Keyu Wang, Zhimei Wang, Xin Huang, Zhaolun Zhang, Wei Li, Ao Liu
article en
1 citations

Abstract

The stereoselective construction of 1,1'-glycosidic linkages represents a significant challenge, as it typically results in a mixture of four possible anomers. Herein, we report a novel and efficient method to achieve this transformation leveraging a remote directing 2-(diphenylphosphinoyl)acetyl (DPPA) group on donors for catalytic glycosylation. This approach provides exceptional dual anomeric stereocontrol for both glycosyl donors and acceptors, which we attribute to the DPPA's role as a powerful hydrogen-bonding (H-bonding) acceptor.

Organic LettersVol. 27(50)
China Pharmaceutical University (CN)
Openalex Percentile: Top 19%
Carbohydrate Chemistry and Synthesis
0.94
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