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Synthesis of cholesterol derivatives based on closo- and nido-carboranes

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Abstract

1-(3-Butyn-1-ylthio)-1,2-dicarba-closo-dodecaborane was synthesized by the alkylation of 1-mercapto-1,2-dicarba-closo-dodecaborane trimethylammonium salt with butyn-3-yl methanesulfonate. The deboronation reaction of this compound gave the corresponding derivative based on nido-carborane, namely, 7-(3-butyn-1-ylthio)-7,8-dicarba-undecaborate anion. 1,4-Disubstituted 1,2,3-triazoles based on closo- and nido-carboranes were synthesized by the CuI-catalyzed 1,3-dipolar [3+2] cycloaddition reaction of the acetylene derivatives of closo- and nido-carboranes with azidocholesterol.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    A. A. Druzina & M. Yu. Stogniy

  2. M. V. Lomonosov Institute of Fine Chemical Technology, MIREA - Russian Technological University, 86 prosp. Vernadskogo, 119571, Moscow, Russian Federation

    M. Yu. Stogniy

Authors
  1. A. A. Druzina
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  2. M. Yu. Stogniy
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Corresponding author

Correspondence to A. A. Druzina.

Additional information

This work was financially supported by the Russian Science Foundation (Project No. 20-73-00228). IR and NMR spectroscopy studies were carried out using the scientific equipment of the X-Ray Structural Center of the A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences with the financial support of the Ministry of Science and Higher Education of the Russian Federation.

This work does not involve human participants and animal subjects.

The authors declare that there is no conflict of interest.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 527–532, March, 2021.

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Druzina, A.A., Stogniy, M.Y. Synthesis of cholesterol derivatives based on closo- and nido-carboranes. Russ Chem Bull 70, 527–532 (2021). https://doi.org/10.1007/s11172-021-3119-1

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  • DOI: https://doi.org/10.1007/s11172-021-3119-1

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