Synthesis and characterization of procyanidin dimers as their peracetates and octamethyl ether diacetates |
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| Institution: | 1. Key Laboratory of Environmental Medicine and Engineering, Ministry of Education, School of Public Health, Southeast University, Nanjing 210009, China;2. Institute of Toxicology and Functional Assessment, Jiangsu Provincial Center for Disease Control and Prevention, Nanjing 210009, China |
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| Abstract: | Condensation of (2R,3S,4R or S)-leucocyanidin or the 5,7,3′,4′-tetramethyl ether of (2R,3R,4S)-leucocyanidin with flavan-3-ols yielded dimeric flavanoids which were converted to their octamethyl ether diacetates, or the deca-acetates for the 2,3-trans-procyanadin series. Comparison is made of the 1H NMR spectra of the deca-acetate and octamethyl ether diacetate derivatives which lead to useful diagnostic shift parameters characteristic of their structures. Condensations afforded a novel biflavanoid with a 3,4-cis-configuration and a triflavanoid of ‘mixed’ stereochemistry. |
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