Stereoselective Synthesis of 2,3‐Diamino‐2,3‐dideoxyglycosides from 3‐O‐Acetyl‐2‐nitroglycals

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Abstract
2‐Nitroglycal is a widely used synthon for aminoglycosides synthesis. Herein, we report an efficient method for 2‐nitroglycals synthesis using nBu4NNO3/Tf2O/DTBMP. Using 3‐O‐acetyl‐2‐nitroglycals as donors, a novel method for the construction of challenging 1,2‐cis‐2,3‐diamino‐2,3‐dideoxyglycosidic linkages was established using 4‐pyrrolidinopyridine (PPY) mediated relay glycosylation reaction. The method enjoys many features, including very mild reaction condition, excellent regio‐ and stereoselectivity, good to excellent yields and broad substrate scope.
Funding Information
  • National Natural Science Foundation of China (21977039, 22007039, 22167015, 22177042)
  • Jiangxi Provincial Department of Science and Technology (jxsq2020101084)

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