Abstract: For the purpose of hunting for better water solubility and anti-tumor activity derivatives, structural modification of anticancer agent β-elemene was reported. Significant heteroatom S and Se were introduced into the skeleton of β-elemene and a pair of bioisosteres 3, 6 were obtained. Whereafter, conjugation with a series of glycosyls selectively gave the corresponding 1,2-trans-glycosides 11a—11c, 12a—12c via several approaches. Then target compounds 13a—13c, 14a—14c were obtained in high yields after deprotection. Heteroatom Se and hydrophilic saccharides were introduced into the skeleton of β-elemene for the first time, and a convenient method was set up for the synthesis of selenide of β-elemene. The glycosylation results demonstrate that glycosyl trichloroacetimidate was a suitable donor for the glycoside synthesis of β-elemene. The structures of products were confirmed via IR, ¹H NMR, ¹³C NMR, ⁷⁷Se NMR and HRMS spectra.

Key words: β-Elemene, Structural modification, Glycoside, Organoselenium