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New carborane-containing amino acids and their derivatives. Crystal structures of n-protected carboranylalaninates

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Abstract

New alanine derivatives containing both the carboranyl and trifluoromethyl groups were synthesized by the reaction of organometallic derivatives of o-carborane with methyl trifluoropyruvate imines. When using the 1R-(−)-menthoxycarbonyl protecting group at the nitrogen atom, one of diastereomers was isolated and characterized. Trifluoromethyl-carboranylalanine methyl esters containing different protecting groups at the nitrogen atom were studied by X-ray diffraction. Both complete and partial deprotection of the amino and carboxy groups was performed.

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References

  1. M. F. Hawthorne, Angew. Chem., Int. Ed. Engl., 1993, 32, 950.

    Article  Google Scholar 

  2. A. H. Soloway, W. Tjarks, B. A. Barnum, F.-G. Rong, R. F. Barth, I. M. Codogni, and J. G. Wilson, Chem. Rev., 1998, 98, 1515.

    Article  CAS  Google Scholar 

  3. N. Sewald and K. Burger, in Fluorine-containing Amino Acids: Synthesis and Properties, Eds V. P. Kukhar’ and V. A. Soloshonok, J. Wiley and Sons, Chichester, 1995, 139.

    Google Scholar 

  4. D. Schirlin, F. Gerhard, J. M. Hornsperger, M. Hamon, J. Wagner, and M. J. Yung, J. Med. Chem., 1988, 31, 30.

    Article  CAS  Google Scholar 

  5. D. E. Zembower, J. A. Gilbert, and M. M. Ames, J. Med. Chem., 1993, 36, 305.

    Article  CAS  Google Scholar 

  6. S. N. Osipov, N. D. Chkanikov, A. F. Kolomiets, and A. V. Fokin, Izv. Akad. Nauk SSSR, Ser. Khim., 1986, 1384 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986, 35, 1256 (Engl. Transl.)].

    Google Scholar 

  7. S. N. Osipov, A. S. Golubev, N. Sewald, T. Michel, A. F. Kolomiets, A. V. Fokin, and K. Burger, J. Org. Chem., 1996, 61, 7521.

    Article  CAS  Google Scholar 

  8. S. N. Osipov, A. F. Kolomiets, and A. V. Fokin, Usp. Khim., 1992, 61, 1457 [Russ. Chem. Rev., 1995, 61, 798 (Engl. Transl.)].

    CAS  Google Scholar 

  9. I. P. Beletskaya, V. I. Bregadze, S. N. Osipov, P. V. Petrovskii, Z. A. Starikova, and S. V. Timofeev, Synlett, 2004, 1247.

  10. Yu. V. Zefirov and P. M. Zorkii, Usp. Khim., 1995, 64, 446 [Russ. Chem. Rev., 1995, 64, 415 (Engl. Transl.)].

    CAS  Google Scholar 

  11. SAINTPlus. Data Reduction and Correction Program, V. 6.01, Bruker AXS, Madison (Wisconsin, USA), 1998.

  12. G. M. Sheldrick, SADABS, V. 2.01, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison (Wisconsin, USA), 1998.

    Google Scholar 

  13. P3 and XDISK. Release 4.1, Siemens AXS, Madison (Wisconsin, USA), 1989.

  14. SHELXTL V. 5.10, Structure Determination Software Suite, Bruker AXS, Madison (Wisconsin, USA), 1998.

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Correspondence to V. I. Bregadze.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 761–767, April, 2007.

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Timofeev, S.V., Bregadze, V.I., Osipov, S.N. et al. New carborane-containing amino acids and their derivatives. Crystal structures of n-protected carboranylalaninates. Russ Chem Bull 56, 791–797 (2007). https://doi.org/10.1007/s11172-007-0118-9

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  • DOI: https://doi.org/10.1007/s11172-007-0118-9

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