Chinese Journal of Organic Chemistry >
Simple and Efficient Synthesis of Pseudoginsenoside HQ
Received date: 2017-03-02
Revised date: 2017-04-07
Online published: 2017-05-02
Supported by
Project supported by the National Natural Science Foundation of China (No. 21502164), the Research Fund for Excellent Young and Middle-age Scientists of Shandong Province (No. BS2015YY039), and the Startup Project of Doctor Scientific Research in Yantai University (No. YX14B17).
Pseudoginsenoside HQ[PHQ, 3β-O-β-D-glucopyranosyl-(20S,24S)-epoxydammarane-12β,25-diol] is the main in vivo metabolite of 20(S)-ginsenoside Rh2 which has high biological activities, with potential medicinal value. The reported chemical synthesis of PHQ suffered complex synthetic route and low overall yield because the rational protecting group strategies were required for the key glycosylation on C-3 position of sapogenins. In this paper, the glycosylation conditions on C-3 position of ocotillol type sapogenins were investigated, and it was found that it could realize the selective glycosylation on C-3-position of sapogenins to prepare PHQ under the Ag2CO3 promoter without the protecting group strategy. A new synthesis of PHQ was achieved in three steps via epoxidation, selective glycosylation and debenzoylation reaction of glycon using commercially available 20(S)-protopanoxadiol as the starting material. This method provides a simple and efficient way for the preparation of PHQ and its derivatives.
Yang Gangqiang , Li Yang , Yang Qing , Yue Xin , Yao Lei , Jiang Yongtao . Simple and Efficient Synthesis of Pseudoginsenoside HQ[J]. Chinese Journal of Organic Chemistry, 2017 , 37(6) : 1530 -1536 . DOI: 10.6023/cjoc201703006
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