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

By Kolio D. Troev

Chemistry and alertness of H-Phosphonates is a superb resource for these making plans the synthesis of recent phosphorus-containing compounds and specifically derivatives containing a phosphonate, phosphoramide or phosphonic acid diester workforce. the wealthy chemistry, cost-effective and simple availability of diesters of H-phosphonic acid makes them a superb selection as synthone in a couple of virtually very important reactions.Phosphonic acid esters are intermediates within the synthesis of significant periods of compounds resembling 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 sessions is reviewed in detail.Alpha-Aminophosphonic acids are a huge classification of biologically energetic compounds, that have acquired 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 ingredients, and as modifiers of typical and artificial polymers. Bisphosphonates are medications which were universal in several bone illnesses, 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 gear. 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 without doubt one of the most important anti-HIV prodrug, that's at present in scientific trials.

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Additional resources for Chemistry and Application of H-Phosphonates

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In this metallo-phosphonate intermediate, the phosphorus atom plays the role of a nucleophile.

Qxd 6/14/2006 4:16 PM Page 52 52 3. Reactivity of H-Phosphonates ozone layer [121]. Chlorofluorohydrocarbons have been proposed as refrigerant substitutes for chlorofluorocarbons [122]. The latter molecules are considered environmentally less harmful because they contain a carbon–hydrogen bond that can be cleaved by chemical reactions at lower altitudes, thereby preventing the compounds from reaching the stratosphere. 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].

In this compound, mobile protons are not present in the ring; H2C H2C O O HC O O OH P P H2C H O H the form with P–OH bond is not observed [56]. Diphenyl H-phosphonate reacts with aliphatic saturated mercaptans and unsaturated mercaptans with the formation of thio and dithio H-phosphonates [59]. O (PhO)2P(O)H PhO- P- SCH2CH3 + CH3CH2SH - PhOH H (PhO)2P(O)H + H2C = CH - CH2SH O PhO- P- SCH2CH = CH2 H O CH2 =CH -CH2S- P- SCH2CH = CH2 H H-phosphonate diesters having double or triple bonds in their alkoxy chains can be synthesized by transesterification of the lower homologues with unsaturated alcohols [60–62].

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