Chiral symmetric phosphoric acid esters as sources of optically active organophosphorus compounds

Kolodiazhnyi, Oleg I.; Grishkun, E. V.; Sheiko, S. G.; Demchuk, Oleg M.; Thoennessen, H.; Jones, Peter G.; Schmutzler, Reinhard

doi:10.1016/s0957-4166(98)00166-9

Cited by 34 publications

(18 citation statements)

References 15 publications

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“…Solvents were purified and dried according to the usual methods. NMR spectra were recorded on a BRUKER AC-200 spectrometer with working frequencies of [14]. HPLC separations were carried out on the "Milichrom-1A" instrument (Russia).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of optically active hydroxyphosphonates

Guliaiko

Nesterov

Sheiko

et al. 2008

Heteroatom Chemistry

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Section: Methodsmentioning

confidence: 99%

Synthesis of optically active hydroxyphosphonates

Guliaiko

Nesterov

Sheiko

et al. 2008

Heteroatom Chemistry

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“…These are alkoxy groups at the phosphorus atom, the ␣-carbon atom, and the substituent at the nitrogen atom. ␣-Aminophosphonates with one, two, or three chiral fragments can be synthesized using commercial chiral reagents such as (R) and (S) ␣-methylbenzylamine, (1S)-endo-(‫-)מ‬borneol, (R)-(‫-)ם‬bornylamine, ‫-)ם(‬ and (‫-)מ‬menthol, and some others [30,31]. So, these compounds are good models for evaluation of transport enantioselectivitystructure relationships.…”

Section: Methodsmentioning

confidence: 99%

Lipophilic aminophosphonates and their calix[4]arene derivatives: synthesis and membrane transport of biorelevant species

et al. 2000

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Many new lipophilic α‐aminophosphonates including macrocyclic (on calix[4]arene platform) and chiral ones were synthesized by the Kabachnik‐Fields reaction. Some of them were examined as carriers for membrane transport of biorelevant species such as hydroxy, amino acids, and amino alcohols. Transport measurements showed that these compounds exhibited remarkable efficiency and selectivity of the transport of very hydrophilic substances across lipophilic membranes. The structures of α‐aminophosphonate‐substrate complexes were investigated by spectral and theoretical methods. © 2000 John Wiley & Sons, Inc. Heteroatom Chem 11:518–527, 2000

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“…The reactions of dialkyl phosphites 21 with benzaldehyde and benzylamine proceed with modest to good stereoselectivity (50-90% d.e.) [94]. Among the numerous methods for the preparation of a-aminophosphonic acids, the most general route is the addition of dialkyl phosphites to Schiffs bases.…”

Section: Amidoalkylation In the Carbonyl Compound-amine-phosphite Thrmentioning

confidence: 99%

Chemistry of Aminophosphonic Acids and Phosphonopeptides

Kukhar

Romanenko

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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Aminophosphonic (and aminophosphinic) acids occupy a prominent position in the understanding of bioprocesses in living organisms and in the construction of new bioregulators -pharmaceuticals and agrochemicals. The so-called phosphorus analogs of the amino acids, aminophosphonic and aminophosphinic acids, are amino acid mimetics in which the carboxylic group is substituted by a phosphonic acid residue P(O)(OH) 2 or phosphinic acid group P(O)(OH)R. The replacement of the carboxylic group by a phosphonic or related moiety results in a number of important consequences: the central atom of a phosphonic acid function consists of an additional substituent that has a tetrahedral configuration in contrast to the planar carbonyl atom of carboxylic group. There are also significant differences in the acidity and steric bulk of these residues. The tetrahedral configuration of the pentavalent phosphorus atom mimics the transition state of the peptide bond cleavage reaction in some enzyme-substrate interactions that is used in the synthesis of new inhibitors. The hydrolytic stability of CÀP bonds is often used in order to prepare stable analogs of bioactive phosphates OÀP(O)(OH) 2 . In addition, aminophosphonic acids and their derivatives are important as metal-complexing agents, which have diagnostic and therapeutic applications, and as industrial chemicals in water treatment, metal extraction, or pollution control.Synthesis, and the chemical, physical, and biological properties of aminophosphonic acids and some directions for their practical application are presented in a number of reviews and book chapters. The most comprehensive account of the chemistry and biology of aminophosphonates and aminophosphinate which covers literature up to 2000 is presented in Kukhar and Hudson ([1] and references therein). Readers are referred to this reference for more detailed information concerning specific aspects of the chemistry and biological activity of aminophosphonic acid derivatives. The purpose of this chapter is to give an updated report on aminophosphonic acids as analogs of amino acids. Numerous heterocyclic compounds that contain both phosphonic and amino groups will not be covered in this report.

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Chiral symmetric phosphoric acid esters as sources of optically active organophosphorus compounds

Cited by 34 publications

References 15 publications

Synthesis of optically active hydroxyphosphonates

Synthesis of optically active hydroxyphosphonates

Lipophilic aminophosphonates and their calix[4]arene derivatives: synthesis and membrane transport of biorelevant species

Chemistry of Aminophosphonic Acids and Phosphonopeptides

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