Synthesis of chiral phosphonobenzaldehydes and phosphonotyrosine
- Authors: Kolodyazhna A.O.1, Grishkun E.V.1, Kolodyazhnyi O.I.1
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Affiliations:
- Institute of Bioorganic Chemistry and Petrochemistry
- Issue: Vol 87, No 5 (2017)
- Pages: 991-996
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/219778
- DOI: https://doi.org/10.1134/S1070363217050176
- ID: 219778
Cite item
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.
About the authors
A. O. Kolodyazhna
Institute of Bioorganic Chemistry and Petrochemistry
Email: olegkol321@rambler.ru
Ukraine, ul. Murmanskaya 1, Kiev, 02094
E. V. Grishkun
Institute of Bioorganic Chemistry and Petrochemistry
Email: olegkol321@rambler.ru
Ukraine, ul. Murmanskaya 1, Kiev, 02094
O. I. Kolodyazhnyi
Institute of Bioorganic Chemistry and Petrochemistry
Author for correspondence.
Email: olegkol321@rambler.ru
Ukraine, ul. Murmanskaya 1, Kiev, 02094