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Synthesis of new chiral derivatives of d-pseudoephedrine

ZHU Honga,MA Yin-jiana,LI Xue-qiang*a,b,c (Ningxia University,a.College of Chemistry and Chemical Engineering;b.Key Laboratory of Energy Sources and Chemical Engineering;c.Development Center of Natural Products and Medication,Yinchuan 750021,China),Huaxue Shiji,2007,29(7),385~388  
The single-structure d-pseudoephedrine was for the first time used as a new nucleophile in the Michael addition-elimination reactions with chiral 5-(S)-alkoxy-3,4-dibromo-2-(5H)-furanone,to synthesize four kinds of new chiral derivatives at yields ranging from 68% to 85%.The research work provided a good supplement to the previous work to make the reaction system of chiral 5-(S)-alkoxy-3,4-dibromo-2-(5H)-furanone and d-pseudoephedrine more perfect.All the target compounds were identified by IR,1HNMR,13CNMR,and HRMS.It showed us a new way to synthesize the single-structure chiral d-pseudoephedrine derivatives,and a basis of new medicine development was founded.
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