Synthesis, structure and properties of betulin D-glycosaminosides

Betulin belongs to the pentacyclic triterpene compounds of the lupan type, similar to lupeol and betulinic acid. Betulin has a high biological activity (viral, antioxidant, anti-inflammatory and anti-can­cer), which contributes to improving the functioning of the human body. Betulin is readily glycosylated, with the primary hydroxyl group at C-28 (–CH₂OH) undergoing a glycosylation reaction more readily than the secondary –OH group at C-3. Currently, I am involved in the synthesis of glycosides, which are built from the rest of betulin and D-glucosamine and D-galactosamine. Betulin glycosides containing amino sugars are not present in nature.[1]

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[1] H. Myszka, D. Grzywacz, M. Zdrowowicz, P. Spisz, K. Butowska, J. Rak, J. Piosik, M. Jaśkiewicz, W. Kamysz, B. Liberek, Design, synthesis and biological evaluation of betulin-3-yl 2-amino-2-deoxy-β-D-glycopyranosides. Bioorg. Chem., 2020, 96, 103568. [https://doi.org/10.1016/j.bioorg.2020.103568]