Chemistry and Application of H-Phosphonates by Kolio D. Troev

By Kolio D. Troev

Chemistry and alertness of H-Phosphonates is a wonderful resource for these making plans the synthesis of latest phosphorus-containing compounds and specifically derivatives containing a phosphonate, phosphoramide or phosphonic acid diester crew. the wealthy chemistry, in your price range and simple availability of diesters of H-phosphonic acid makes them an exceptional selection as synthone in a couple of essentially very important reactions.Phosphonic acid esters are intermediates within the synthesis of significant periods of compounds comparable to alpha-aminophosphonic acids, bisphosphonates, epoxyalkylphosphonates, alpha-hydroxyalkylphosphonates, phosphoramides, poly(alkylene H-phosphonate)s, poly(alkylene phosphate)s, nucleoside H-phosphonates. The synthesis of every of those compound periods is reviewed in detail.Alpha-Aminophosphonic acids are an enormous type of biologically energetic compounds, that have obtained an expanding volume of consciousness simply because they're thought of to be structural analogues of the corresponding Alpha-amino acids. The utilities of alpha-aminophosphonates as peptide mimics, haptens of catalytic antibodies, enzyme inhibitors, inhibitors of cancers, tumours, viruses, antibiotics and pharmacologic brokers are good documented. Alpha-Hydroxyalkanephosphonates are compounds of vital organic and medicinal purposes. Dialkyl epoxyalkylphosphonates are of curiosity as a result of their use as intermediates within the synthesis of bioactive components, and as modifiers of normal and artificial polymers. Bisphosphonates are medicines which were typical in several bone ailments, and feature lately been used effectively opposed to many parasites. Poly(alkylene H-phosphonate)s and poly(alkylene phosphate)s are promising, biodegradable, water soluble, new polymer-carriers of substances. Nucleoside H-phosphonates appear to be the main beautiful applicants as beginning fabrics within the chemical synthesis of DNA and RNA fragments. The 5'-hydrogen phosphonate-3'-azido-2',3'-dideoxythimidine is likely one of the most important anti-HIV prodrug, that is at present in medical trials.

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O O O CH3O- P - OCH3 + CH3COOH - CH3COOCH3 H CH3O- P - OH + CH3COOH HO- P - OH - CH3COOCH3 H H This two-stage equilibrium can be successfully shifted toward the formation of H-phosphonic acid by removing the formed methyl acetate by distillation. 6 SUBSTITUTION REACTIONS AT THE PHOSPHORUS ATOM The strongly polar character of the phosphoryl group of the H-phosphonates is responsible to a great extent for the reactivity of this class of organophosphorus compounds. 1 Transesterification reaction The charge distribution in the molecule of dimethyl H-phosphonate obtained with Milliken population analysis clearly indicates that the electron density at the phosphorus atom is the lowest, that is, the phosphorus atom is an electrophilic center.

The Atherton–Todd reaction of halocarbons with dialkyl H-phosphonates is one potentially useful reaction that can be used to carry out such transformation under homogeneous conditions [123]. 4 Hz. The experimentally found order of reactivity to dialkyl phosphonates follows the sequence CCl4 Ͼ CFCl3 Ͼ CF2Cl2, and no reaction has been reported yet at a carbon atom that also contains a carbon–hydrogen bond. Direct azidation, cyanation, and thiocyanation of diesters of H-phosphonic acid were accomplished readily with sodium pseudohalides in acetonitrile under mild modified Atherton–Todd conditions [124].

Subsequently, it has been shown that phosphonates occur naturally in a variety of organisms. Consequently, there is a growing need to develop new and efficient synthetic methods for preparation of organophosphorus compounds bearing a P–C bond. Phosphonates are more reactive than the corresponding phosphate esters because the carbon atom has no unpaired electrons for a p –d contribution to the C–P bond [135]. This makes the phosphorus atom of phosphonates more electrophilic than the phosphorus atom of the corresponding phosphate ester.

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