Synthesis of chiral phosphonobenzaldehydes and phosphonotyrosine
- 作者: Kolodyazhna A.1, Grishkun E.1, Kolodyazhnyi O.1
-
隶属关系:
- Institute of Bioorganic Chemistry and Petrochemistry
- 期: 卷 87, 编号 5 (2017)
- 页面: 991-996
- 栏目: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/219778
- DOI: https://doi.org/10.1134/S1070363217050176
- ID: 219778
如何引用文章
详细
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.
作者简介
A. Kolodyazhna
Institute of Bioorganic Chemistry and Petrochemistry
Email: olegkol321@rambler.ru
乌克兰, ul. Murmanskaya 1, Kiev, 02094
E. Grishkun
Institute of Bioorganic Chemistry and Petrochemistry
Email: olegkol321@rambler.ru
乌克兰, ul. Murmanskaya 1, Kiev, 02094
O. Kolodyazhnyi
Institute of Bioorganic Chemistry and Petrochemistry
编辑信件的主要联系方式.
Email: olegkol321@rambler.ru
乌克兰, ul. Murmanskaya 1, Kiev, 02094