Synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue |
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Authors: | Wang Peng Li Chunxia Zang Jing Song Ni Zhang Xiuli Li Yingxia |
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Institution: | Key Laboratory of Marine Drugs, Ministration of Education, Marine Drug and Food Institute, Ocean University of China, Qingdao. |
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Abstract: | The focus of this work was on the synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue. Therefore, 3-O-{beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-beta-D-glucopyranosyl] ester 1 was concisely synthesized by two strategies in 22% and 41% overall yield, respectively, and another congener 3-O-{beta-D-xylopyranosyl-(1-->2)]-beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-beta-D-glucopyranosyl] ester 2 was also efficiently prepared in 81% overall yield. The (1)H NMR and (13)C NMR signals of saponin 2 are all consistent with those reported for the natural product. |
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Keywords: | Ursolic acid Saponin Glycosylation Synthesis |
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