222639-43-2Relevant academic research and scientific papers
Collective syntheses of phenylethanoid glycosides by interrupted Pummerer reaction mediated glycosylations
Zhao, Yueqi,Zeng, Jing,Liu, Yan,Xiao, Xiong,Sun, Guangfei,Sun, Jiuchang,Shu, Penghua,Fu, Dengxian,Meng, Lingkui,Wan, Qian
, p. 471 - 497 (2018)
The collective total syntheses of nine natural phenylethanoid glycosides (PhEGs) together with proposed Incanoside B in a divergent mode were described. By using a core disaccharide as common intermediate, our developed interrupted Pummerer reaction media
Remote Activation of Disarmed Thioglycosides in Latent-Active Glycosylation via Interrupted Pummerer Reaction
Xiao, Xiong,Zhao, Yueqi,Shu, Penghua,Zhao, Xiang,Liu, Yan,Sun, Jiuchang,Zhang, Qian,Zeng, Jing,Wan, Qian
supporting information, p. 13402 - 13407 (2016/10/22)
S-glycosides, S-2-(2-propylthio)benzyl (SPTB) glycosides, were converted to the corresponding oxidized glycosyl donors, S-2-(2-propylsulfinyl)benzyl (SPSB) glycosides, by simple and selective oxidation. Treatment of disarmed SPSB donor and various acceptors with triflic anhydride provided the desired glycosides in good to excellent yields. Meanwhile, observation of thiosulfinate, thiosulfonate, and disulfide suggested that the leaving group was activated via an interrupted Pummerer reaction. The disarmed SPSB thioglycosyl donors could be selectively activated in the presence of various thioglycosides with remote activation mode. Finally, two natural hepatoprotective glycosides, Leonoside E and Leonuriside B, were efficiently synthesized in a convergent manner with this newly developed method.
