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Synthesis of C-29-phosphonium derivatives of 3,28-diacetoxylup-20(29)-en-30-oic acid

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Abstract

3β,28-Diacetoxylup-20(29)-en-30-oic acid (obtained via oxidation of betulin diacetate) enters the addition reaction with P—H-phosphonium salts (triarylphosphonium trifluoroacetates) under mild conditions to afford β-carboxyalkylphosphonium salts. Structure and composition of the resulting compounds were confirmed by NMR and IR spectroscopy, mass spectrometry, and elemental analysis.

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Authors and Affiliations

  1. A. M. Butlerov Institute of Chemistry, Kazan (Volga region) Federal University, 18 ul. Kremlyovskaya, 420008, Kazan, Russian Federation

    D. V. Ponomaryov, L. R. Grigor´eva, A. V. Nemtarev, O. V. Tsepaeva, V. F. Mironov & I. S. Antipin

  2. A. E. Arbuzov of Organic and Physical Chemistry, Federal Research Center ″Kazan Scientific Center of the Russian Academy of Sciences″, 8 ul. Arbuzova, 420008, Kazan, Russian Federation

    A. V. Nemtarev, O. V. Tsepaeva, V. F. Mironov & I. S. Antipin

Authors
  1. D. V. Ponomaryov
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  2. L. R. Grigor´eva
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  3. A. V. Nemtarev
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  4. O. V. Tsepaeva
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  5. V. F. Mironov
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  6. I. S. Antipin
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Corresponding author

Correspondence to A. V. Nemtarev.

Additional information

Synthetic part of the present study was financially supported by the Russian Foundation for Basic Research (Project No. 19-33-90275), spectral studies were supported by the Ministry of Science and Higher Education of the Russian Federation (subsidies allocated to Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences” (FRS KSC RAS) and Kazan Federal University for the state assignements in the field of scientific activities). The authors gratefully acknowledge the Assigned Spectral Analytical Center for Study of Structure, Properties and Composition of Substances and Materials of the KSC RAS.

Based on the materials of the International Markovnikov Congress on Organic Chemistry (June 21-28, 2019, Moscow-Kazan, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0487—0491, March, 2020.

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Ponomaryov, D.V., Grigor´eva, L.R., Nemtarev, A.V. et al. Synthesis of C-29-phosphonium derivatives of 3,28-diacetoxylup-20(29)-en-30-oic acid. Russ Chem Bull 69, 487–491 (2020). https://doi.org/10.1007/s11172-020-2787-6

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  • DOI: https://doi.org/10.1007/s11172-020-2787-6

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