Kolodiazhna A. Asymmetric synthesis of hydroxyphosphonates and their derivatives with potential biological activity

Українська версія

Thesis for the degree of Candidate of Sciences (CSc)

State registration number

0409U000858

Applicant for

Specialization

  • 02.00.10 - Біоорганічна хімія

27-02-2009

Specialized Academic Board

Д 26.220.01

V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine

Essay

Optically active hydrophosphonic acids derivatives. Development of new methods for the asymmetric synthesis of hydrophosphonates and synthesis of their representatives being potentially biologically active substances. Chemical synthesis, column and tinlight chromatography, IR-and PMR-spectroscopy, mass-spectrometry, X-ray research. Preparative method for the synthesis of functionalized phosphonates by reaction of С=Х nucleophiles, with reactive pair trialkylphosphite/pyridin halogenohydrate was proposed and a new method for the synthesis of chiral alkyliodides by reaction of chiral alcohol with bis(diethylamino)phosphite and ethyl iodide was developed. Examples of double and triple stereoselectivity were found and studied; alkaloids as asymmetric catalysts for the phosphaaldol reaction were studied. Chiral methylene-bisphosphonates were synthesized for the first time. Chiral diols as potential ligands for transition metal complexes were synthesized; bis(amino)phosphonates as potential biologically active compounds were synthesised. Chiral phosphonic analogues of natural threonic acids, erythrose and phosphatidic acids were prepared. Sphere of use - bioorganic and organic chemistry.

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