Stereoselective Synthesis of 2-Deoxy-β-O-Aryl Glycosides by a One-Pot Strategy Involving C─O Coupling and
Yang-He Wang1, You-Hong Niu1, Qin Li1
1State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, and Chemical Biology Center, Peking University, Xue Yuan Road No. 38, Beijing, 100191, China.
This study introduces a new one-pot method for synthesizing 2-deoxy-β-O-aryl glycosides, crucial anticancer and antibacterial compounds. The efficient copper-catalyzed coupling and reduction strategy achieves high yields and exclusive β-stereoselectivity.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Synthetic Chemistry
Background:
- 2-deoxy-β-O-aryl glycosides are vital anticancer and antibacterial agents.
- Direct synthesis methods often yield undesired α-anomers, limiting efficiency.
Purpose of the Study:
- To develop a novel, efficient one-pot synthesis for 2-deoxy-β-O-aryl glycosides.
- To achieve exclusive β-stereoselectivity in the synthesis of these important compounds.
Main Methods:
- Utilized a Cu(I)-catalyzed C─O cross-coupling reaction between 1-iodoglycals and phenols.
- Performed in situ reduction of ketene acetals using catecholborane for the one-pot procedure.
Main Results:
- Successfully synthesized a wide range of 2-deoxy-β-O-aryl glycosides with high yields.
- Achieved exclusive β-stereoselectivity, overcoming limitations of previous methods.
- Demonstrated applicability in late-stage modification of bioactive natural products and drugs.
Conclusions:
- The developed one-pot protocol offers an efficient and stereoselective route to valuable 2-deoxy-β-O-aryl glycosides.
- This strategy enhances the synthesis of important pharmaceutical compounds and facilitates late-stage functionalization.
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