α-Hydroxyphosphonates as versatile starting materials

Rádai, Zita

doi:10.1080/10426507.2018.1544132

Cited by 17 publications

(13 citation statements)

References 79 publications

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“…In another method, the synthesis of hydroxyphosphonates has been reported from the reaction of carbonyl compounds with the addition of nucleophilic trialkyl phosphate ( Vasikaran, 2001 ). In general, both reactions are performed in the presence of a catalyst and in some cases in the presence of the base ( Radai 2019 ) ( Radai and Keglevich 2018b ). In recent years, enantiomerically pure hydroxyphosphonates have been synthesized by chiral-resolving agents or asymmetric chiral synthesis ( Rádai et al, 2018a ; Kaboudin et al, 2019a ).…”

Section: Synthetic Methods For the Preparation Of Hydroxy- And Amino-...mentioning

confidence: 99%

Hydroxy- and Amino-Phosphonates and -Bisphosphonates: Synthetic Methods and Their Biological Applications

et al. 2022

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Phosphonates and bisphosphonates are stable analogs of phosphates and pyrophosphates that are characterized by one and two carbon–phosphorus bonds, respectively. Among the various phosphonates and bisphosphonates, hydroxy and amino substitutes are of interest as effective in medicinal and industrial chemistry. For example, hydroxy bisphosphonates have proven to be effective for the prevention of bone loss, especially in osteoporotic disease. On the other hand, different substitutions on the carbon atom connected to phosphorus have led to the synthesis of many different hydroxy- and amino-phosphonates and -bisphosphonates, each with its distinct physical, chemical, biological, therapeutic, and toxicological characteristics. Dialkyl or aryl esters of phosphonate and bisphosphonate compounds undergo the hydrolysis process readily and gave valuable materials with wide applications in pharmaceutical and agriculture. This review aims to demonstrate the ongoing preparation of various classes of hydroxy- and amino-phosphonates and -bisphosphonates. Furthermore, the current review summarizes and comprehensively describes articles on the biological applications of hydroxyl- and amino-phosphonates and -bisphosphonates from 2015 until today.

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Section: Synthetic Methods For the Preparation Of Hydroxy- And Amino-...mentioning

confidence: 99%

Hydroxy- and Amino-Phosphonates and -Bisphosphonates: Synthetic Methods and Their Biological Applications

et al. 2022

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“…α-Hydroxyphosphonates, particularly the bis-α-hydroxyphosphonate version, are useful organophosphorus compounds with multifaceted pharmaceutical activities, flame-retardant properties and synthetic applications. [114][115][116][117][118][119] Recently, Mou et al accomplished a metal-free green method to prepare bis-αhydroxyphosphonates 31 via an atom-economical Pudovik reaction between aromatic/heteroaromatic dialdehydes 30 and dialkyl phosphonates using triethylamine as catalyst (Scheme 26). 120 The reaction proceeded smoothly under mild conditions with high activity, atom economy, and operational simplicity.…”

Section: Synthesis Of Miscellaneous Organophosphorus Compoundsmentioning

confidence: 99%

Green-inspired synthetic drives for organophosphorus compounds under solvent-free conditions

Brahmachari¹,

Karmakar²

2022

Arkivoc

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Organophosphorus chemistry is an exciting field of research. Phosphorus-functionalized organic molecules find practical and useful applications in such diverse areas as medicinal, pharmaceutical, agrochemical, and materials chemistries, both on laboratory and industrial scales. Green-chemistry principles are motivating the design and development of newer synthetic methodologies for such beneficial organophosphorus compounds and their analogues. Solvent-free conditions are associated with several practical benefits, including operational simplicity, cost-effectiveness, minimization of waste generation, and reduced pollution, all of which are very much crucial for industrial process development. This review summarizes solvent-free synthetic methodologies for functionalized organophosphorus compounds reported during the period 2016 through 2021.

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“…Despite the fact that the biological activity of carboxyhydroxyphosphonates is unknown, pure enantiomers of these compounds may be used as chiral auxiliaries, useful in 31 P NMR spectroscopy to determine the enantiomeric purity and absolute configuration of different classes of compounds [18]. Moreover, they can be used as precursors of aminophosphonates [12], due to the fact that many of aminophosphonic acids are biologically active [19]. Dimethyl 1carboxy-1-hydroxymethylphosphonate can be transformed to its (4-nitrophenyl)methyl ester, which can be used in the synthesis of 2-substitued-3-carboxy carbapenem antibiotics [20].…”

Section: Synthesis Of Enzymatic Hydrolysis Substratesmentioning

confidence: 99%

“…Hydroxyphosphonates are among the countless different classes of compounds obtained by enantioselective biocatalysis [9,10]. These compounds have a wide range of biological properties, serving as antibacterial, antiviral, and anticancer agents, as well as enzyme inhibitors or pesticides; they can also be used as precursors of other biologically active compounds [11][12][13][14]. Their bioavailability depends on their three-dimensional structure; therefore, obtaining them as enantiopure isomers with a specific absolute configuration is crucial for therapeutic effectiveness and drug safety [15].…”

Section: Introductionmentioning

confidence: 99%

Lipase-Catalyzed Kinetic Resolution of Dimethyl and Dibutyl 1-Butyryloxy-1-carboxymethylphosphonates

Majewska

2021

Catalysts

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The main objective of this study is the enantioselective synthesis of carboxyhydroxyphosphonates by lipase-catalyzed reactions. For this purpose, racemic dimethyl and dibutyl 1-butyryloxy-1-carboxymethylphosphonates were synthesized and hydrolyzed, using a wide spectrum of commercially available lipases from different sources (e.g., fungi and bacteria). The best hydrolysis results of dimethyl 1-butyryloxy-1-carboxymethylphosphonate were obtained with the use of lipases from Candida rugosa, Candida antarctica, and Aspergillus niger, leading to optically active dimethyl 1-carboxy-1-hydroxymethylphosphonate (58%–98% enantiomeric excess) with high enantiomeric ratio (reaching up to 126). However, in the case of hydrolysis of dibutyl 1-butyryloxy-1-carboxymethylphosphonate, the best results were obtained by lipases from Burkholderia cepacia and Termomyces lanuginosus, leading to optically active dibutyl 1-carboxy-1-hydroxymethylphosphonate (66%–68% enantiomeric excess) with moderate enantiomeric ratio (reaching up to 8.6). The absolute configuration of the products after biotransformation was also determined. In most cases, lipases hydrolyzed (R) enantiomers of both compounds.

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α-Hydroxyphosphonates as versatile starting materials

Cited by 17 publications

References 79 publications

Hydroxy- and Amino-Phosphonates and -Bisphosphonates: Synthetic Methods and Their Biological Applications

Hydroxy- and Amino-Phosphonates and -Bisphosphonates: Synthetic Methods and Their Biological Applications

Green-inspired synthetic drives for organophosphorus compounds under solvent-free conditions

Lipase-Catalyzed Kinetic Resolution of Dimethyl and Dibutyl 1-Butyryloxy-1-carboxymethylphosphonates

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