Synthesis of Pro-XylaneTM: A new biologically active C-glycoside in aqueous media

The scope and limitation of Lubineau’s reaction were evaluated for the synthesis of C-glycosides (compounds 1–13). Further transformation of side chain carbonyl was also achieved (compounds 16–23). Optimization of these two steps was investigated in xylose case. Some of the compounds were shown to stimulate sulfated glycosaminoglycans (GAGs) synthesis. Compound 20 (called Pro-XylaneTM) was identified as the best activator of GAGs biosynthesis. Pro-XylaneTM was developed using environmentally friendly conditions relevant to ‘Green-Chemistry’ principles and launched on the market in September 2006. This compound is the first example of ‘Green’ chemical used in cosmetic.

Graphical abstractThe scope and limitation of Lubineau’s reaction were evaluated for the synthesis of C-glycosides. Further transformation of side chain carbonyl was also achieved. Optimization of these two steps was investigated in xylose case. Some of the compounds were shown to stimulate sulfated glycosaminoglycans (GAGs) synthesis. Pro-XylaneTM was identified as the best activator of GAGs biosynthesis.Figure optionsDownload full-size imageDownload as PowerPoint slide