Stereoselective Synthesis of 2,3‐Diamino‐2,3‐dideoxyglycosides from 3‐<i>O</i>‐Acetyl‐2‐nitroglycals
Xiaopei Wu, Zhichao Zheng, Liming Wang, Yunxia Xue, Jin‐Xi Liao, Hui Liu, D. Liu, Jiansong Sun, Qingju Zhang
Abstract
Abstract 2‐Nitroglycal is a widely used synthon for aminoglycosides synthesis. Herein, we report an efficient method for 2‐nitroglycals synthesis using n Bu 4 NNO 3 /Tf 2 O/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.
Topics & Concepts
SynthonChemistryStereoselectivityGlycosylationStereochemistrySubstrate (aquarium)Combinatorial chemistryReaction conditionsRegioselectivityOrganic chemistryCatalysisBiochemistryOceanographyGeologyCarbohydrate Chemistry and SynthesisPneumocystis jirovecii pneumonia detection and treatmentPeptidase Inhibition and Analysis