Abstract
A convenient method for the synthesis of C(28)-linker derivatives of triterpenoids containing a phosphonate group is presented. The method is based on the reaction of triterpenic acids (using betulinic acid as an example) with O, O-dialkyl-ω-bromoalkane phosphonates in DMF in the presence of K2CO3. The target phosphonates are synthesized in a yield of about 80%. The structures and compositions of the synthesized compounds were confirmed by NMR spectroscopy, IR spectroscopy, and elemental analysis.
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The authors are grateful to the staff of the Collective Spectral Analytical Center for Investigation of Structure, Properties and Composition of Substances at the Federal Research Center “Kazan Scientific Center of Russian Academy of Sciences.”
This work was financially supported by the Russian Foundation for Basic Research (Project No. 20-33-70194; synthesis of compounds) and subsided by the Federal Research Center “Kazan Scientific Center of Russian Academy of Sciences” and Kazan Federal University in terms of the state assignment in the sphere of scientific activity (state assignment No. 0671-2020-0063; spectral studies).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 179–182, January, 2021.
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Tsepaeva, O.V., Nemtarev, A.V., Grigor’eva, L.R. et al. Synthesis of C(28)-linker derivatives of betulinic acid bearing phosphonate group. Russ Chem Bull 70, 179–182 (2021). https://doi.org/10.1007/s11172-021-3074-x
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DOI: https://doi.org/10.1007/s11172-021-3074-x