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Synthesis of chiral phosphonobenzaldehydes and phosphonotyrosine

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Abstract

A method for obtaining of chiral phosphonobenzaldehydes has been developed. The Abramov reaction between dimenthyl phosphite and 4-diethoxymethylbenzaldehyde followed by separation of stereoisomers has yielded enantiomerically pure (1S)- and (1R)-1-hydroxyphosphonates. The resulting phosphonates, after removal of acetal protection, have been converted to (1S)- and (1R)-1-hydroxymethylphosphonobenzaldehydes. By reacting with (diethylamino)trifluorosulfurane, 1-hydroxyphosphonates have been converted to 4-(1-fluoromethyl)phosphonobenzaldehydes. The synthesized chiral phosphonobenzaldehydes are convenient chiral reactants for the preparation of phosphorus analogs of natural compounds, as has been shown with the example of synthesis of the phosphonium analog of phosphotyrosine.

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References

  1. Li, P., Zhang, M., Peach, M.L., Liu, H., Yang, D., and Roller, P.P., Org. Lett., 2003, vol. 5, no. 17, p. 3095. doi 10.1021/ol035078+

    Article  CAS  Google Scholar 

  2. Gulyaiko, I.V. and Kolodyazhnyi O.I., Russ. J. Gen. Chem., 2009, vol. 79, no. 1, p. 148. doi 10.1134/S1070363209010277

    Article  CAS  Google Scholar 

  3. Tulsi, N.S., Downey, A.M., and Cairo, C.W., Bioorg. Med. Chem., 2010, vol. 18, no. 24, p. 8679. doi 10.1016/j.bmc.2010.09.040

    Article  CAS  Google Scholar 

  4. Burke, T.R., Smyth, M.S., Nomizu, M., Otaka, A., and Roller, P.P., J. Org. Chem., 1993, vol. 58, no. 6, p. 1336. doi 10.1021/jo00058a009

    Article  CAS  Google Scholar 

  5. Smith, M.S., Ford, H., Jr., and Burke, T.R., Jr., Tetrahedron Lett., 1992, vol. 33, no. 29, p. 4137. doi 10.1016/S0040-4039(00)74672-7

    Article  Google Scholar 

  6. Kolodiazhnyi, O.I., Tetrahedron. Asymmetry, 2005, vol. 16, no. 20, p. 3295. doi 10.1016/j.tetasy.2005.09.007

    Article  CAS  Google Scholar 

  7. Dale, J.A. and Mosher, H.S., J. Am. Chem. Soc., 1973, vol. 95, no. 2, p. 512. doi 10.1021/ja00783a034

    Article  CAS  Google Scholar 

  8. Kolodyazhnyi, O.I., Kolodyazhnaya, A.O., and Kukhar’, V.P., Russ. J. Gen. Chem., 2006, vol. 76, no. 8, p. 1342. doi 10.1134/S1070363206080354

    Article  CAS  Google Scholar 

  9. Knittel, D., Synthesis, 1985, no. 1, p. 186. doi 10.1055/s-1985-31149

    Article  Google Scholar 

  10. Krause, D. and Van Etten, R., New England J. Med., 2005, vol. 353, no. 2, p. 172. doi 10.1056/NEJMra044389

    Article  CAS  Google Scholar 

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Correspondence to O. I. Kolodyazhnyi.

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Original Russian Text © A.O. Kolodyazhna, E.V. Grishkun, O.I. Kolodyazhnyi, 2017, published in Zhurnal Obshchei Khimii, 2017, Vol. 87, No. 5, pp. 801–806.

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Kolodyazhna, A.O., Grishkun, E.V. & Kolodyazhnyi, O.I. Synthesis of chiral phosphonobenzaldehydes and phosphonotyrosine. Russ J Gen Chem 87, 991–996 (2017). https://doi.org/10.1134/S1070363217050176

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  • DOI: https://doi.org/10.1134/S1070363217050176

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