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Synthesis of bidesmosidic dihydrodiosgenin saponins bearing a 3-O-beta-chacotriosyl moiety
Authors:Zhang Yichun  Li Yingxia  Zhu Shilei  Guan Huashi  Lin Feng  Yu Biao
Institution:Marine Drugs and Food Institute, Ocean University of China, Qingdao 266003, China.
Abstract:3-O-beta-Chacotriosyl-26-O-beta-D-glucopyranosyl-(25R)-furost-5-en (1), a mimic of the antitumor active proto-dioscin, was concisely synthesized from diosgenin in a linear nine steps and in 17% overall yield. Its congeners with a alpha-l-rhamnopyranosyl, beta-lactosyl, or without a substituent at the 26-OH (13-15) were also prepared. Compound 1, as well as 13-15, did not show any inhibition against tumor cells, implying that proto-dioscin might be also inactive, but readily converted into the antitumor active dioscin.
Keywords:TBDMS  tert-butyldimethylsilyl-  TBDPS  tert-butyldiphenylsilyl-  1-BBTZ  1-(benzoyloxy)benzotriazole  TBAF  tetrabutylammonium fluoride  DMAP  4-(dimethylamino)pyridine  SRB  sulforhodamine B
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