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Preparation of enantiomerically pure (S)-2-hydroxy heptanoate via bakers' yeast catalyzed hydrolytic resolution

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Summary

2-Hydroxyheptanoic esters could be optically resolved up to ≥99% ee by bakers' yeast mediated enantioselective hydrolysis. Of various esters tested, ethyl ester was proved to be the best substrate. The esteratic activity was completely inhibited by butylsulfonyl-fluoride.

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References

  • Brown, H. C., Cho, B. T. and Park, W. S. (1986).J. Org. Chem. 51, 3398–3400.

    Google Scholar 

  • Caton, M. P. L. (1979).Tetrahedron 35, 2705–2742.

    Google Scholar 

  • Clarke, H. T. and Taylor, E. R. (1943).Org. Syn. Coll. Vol. 1, 115–116.

    Google Scholar 

  • Corey, E. J., Shirahama, H., Yamamoto, H., Terashima, S., Venkateswarlu, A. and Schaaf, T. K. (1971).J. Am. Chem. Soc. 93, 1490–1491.

    Google Scholar 

  • Dale, J. A., Dull, D. L. and Mosher, H. S. (1969).J. Org. Chem. 34, 2543–2549.

    Google Scholar 

  • de Montarby, L., Mosset, P. and Gree, R. (1988).Tetrahedron Lett. 29, 3937–3940.

    Google Scholar 

  • Fadnavis, N. W., Reddy, N. P. and Bhalerao, U. T. (1989).J. Org. Chem. 54, 3218–3221.

    Google Scholar 

  • Fahrney, D. E. and Gold, A. M. (1963).J. Am. Chem. Soc. 85, 997–1000.

    Google Scholar 

  • Glanzer, B. I., Faber, K. and Griengl, H. (1986).Tetrahedron Lett. 27, 4293–4296.

    Google Scholar 

  • Glanzer, B. I., Faber, K. and Griengl, H. (1987).Tetrahedron 43, 771–778; 5791–5796.

    Google Scholar 

  • Hauser, E. M., Coleman, M. L., Huffman, R. C. and Carroll, F. I. (1974).J. Org. Chem. 39, 3426–3427.

    Google Scholar 

  • Horn, D. H. S. and Pretorius, Y. Y. (1954).J. Chem. Soc., 1460–1464.

  • Nakamura, K., Inoue, K., Ushio, K., Oka, S. and Ohno, A. (1988).J. Org. Chem. 53, 2589–2593.

    Google Scholar 

  • Nugteren, D. H., van Dorp, D. A., Bergstrom, S., Hamberg, M. and Samuelsson, B. (1966).Nature 212, 38–39.

    Google Scholar 

  • Sasaki, T., Nakagawa, Y., Takahashi, J., Iwabuchi, K. and Ishii, K. (1984).Chem. Lett., 263–264.

  • Sih, C. J., Salomon, R. G., Price, P., Peruzzoti, G. and Sood, R. (1972).J. Chem. Soc., Chem. Commun., 240–241.

  • Sih, C. J. and Wu, S.-H. (1989).Topics in Stereochemistry 19, 63–125.

    Google Scholar 

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Authors and Affiliations

  1. Department of Industrial Chemistry, Niihama National College of Technology, Yakumo, 792, Niihama Ehime, Japan

    Kazutoshi Ushio, Shyoji Yamauchi & Kyoko Masuda

Authors
  1. Kazutoshi Ushio
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  2. Shyoji Yamauchi
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  3. Kyoko Masuda
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Ushio, K., Yamauchi, S. & Masuda, K. Preparation of enantiomerically pure (S)-2-hydroxy heptanoate via bakers' yeast catalyzed hydrolytic resolution. Biotechnol Lett 13, 495–500 (1991). https://doi.org/10.1007/BF01049206

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  • DOI: https://doi.org/10.1007/BF01049206

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