Dual Anomeric Stereocontrol in 1,1'-Glycosylation via a Remote Directing 2-(Diphenylphosphinoyl)acetyl Group
Xin Huang1, Keyu Wang1, Zhaolun Zhang1
1Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, 639 Longmian Avenue, Nanjing, Jiangsu 211198, China.
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.
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