Synthesis of furanosyl α-C-glycosides derived from 4-chloro-4-deoxy-α-d-galactose and their cytotoxic activities

Condensation of a new unnatural sugar 1 with 1,3-dicarbonyl compounds in the presence of anhydrous zinc chloride gave the polyhydroxyalkyl-furans in excellent yields. Further modification afforded the corresponding furanosyl α-C-glycoside derivatives. The absolute configuration of 3-acetyl-2-methyl-5-(2′-chloro-d-galacto-tetritol-1-yl)-furan was confirmed by single-crystal X-ray analysis. The in vitro cytotoxic activities of these furanosyl C-glycosides were also investigated.

Graphical abstractSome new furanosyl α-C-glycoside derivatives were synthesized and tested for in vitro cytotoxicity against human lung adenocarcinoma cell lines.Figure optionsDownload full-size imageDownload as PowerPoint slide