Wang Peng, Li Chunxia, Zang Jing, Song Ni, Zhang Xiuli, Li Yingxia
Key Laboratory of Marine Drugs, Ministration of Education, Marine Drug and Food Institute, Ocean University of China, Qingdao.
Carbohydr Res. 2005 Sep 26;340(13):2086-96. doi: 10.1016/j.carres.2005.06.024.
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.
这项工作的重点是合成两种带有2,3-分支三糖残基的双糖苷型熊果酸皂苷。因此，分别通过两种策略简洁地合成了3-O-{[β-D-吡喃葡萄糖基-(1→2)]-[α-L-吡喃阿拉伯糖基-(1→3)]-α-L-吡喃阿拉伯糖基}熊果酸-28-O-[β-D-吡喃葡萄糖基]酯1，总产率分别为22%和41%，并且另一种同系物3-O-{[β-D-吡喃木糖基-(1→2)]-[β-D-吡喃葡萄糖基-(1→3)]-α-L-吡喃阿拉伯糖基}熊果酸-28-O-[β-D-吡喃葡萄糖基]酯2也以81%的总产率高效制备。皂苷2的¹H NMR和¹³C NMR信号与天然产物报道的信号均一致。
