7598-61-0

Usage

Uses

Used in Organic Chemistry:
DIETHYL 2,2-DIETHOXYETHYLPHOSPHONATE is used as a Wittig reagent for the synthesis of α,β-alkenal derivatives by two-carbon homologation. This reagent is valuable in the preparation of complex organic molecules and pharmaceutical compounds.
Used in Calixarene Synthesis:
In the field of supramolecular chemistry, DIETHYL 2,2-DIETHOXYETHYLPHOSPHONATE is used as a reactant for the synthesis of lower rim-phosphonylated rexorcinol calix[4]arenes through condensation reactions. These calixarenes have potential applications in molecular recognition and sensing.
Used in Radical Chemistry:
DIETHYL 2,2-DIETHOXYETHYLPHOSPHONATE is utilized as a reactant for the synthesis of α-Phosphovinyl radicals via a radical trapping sequence. This allows for the generation of reactive intermediates that can be employed in various chemical transformations.
Used in Medicinal Chemistry:
This phosphonate compound is used as a reactant for the synthesis of inhibitors of reverse transcriptase via 1,3-dipolar cycloadditions. These inhibitors are important in the development of antiviral drugs, particularly against retroviruses.
Used in Heterocyclic Chemistry:
DIETHYL 2,2-DIETHOXYETHYLPHOSPHONATE is employed as a reactant for Friedel-Crafts reactions, which are essential in the synthesis of a wide range of heterocyclic compounds with potential applications in pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C10H23O5P/c1-5-12-10(13-6-2)9-16(11,14-7-3)15-8-4/h10H,5-9H2,1-4H3

Upstream product

• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 122-52-1 triethyl phosphite 
• 621-62-5 chloroacetaldehyde diethyl acetal 

Downstream Products

• 1606-75-3 (2-oxoethyl)phosphonic acid diethyl ester 
• 99624-20-1 hexaethyl benzene-1,3,5-tris(phosphonate) 
• 85071-64-3 dibuthyl phosphonoacetaldehyde 
• 208511-62-0 N-[(E)-2-diethoxyphosphorylethylideneamino]-4-methyl-benzenesulfonamide 
• 79782-60-8 <2-<(phenylmethyl)amino>ethenyl>phosphonic acid diethyl ester 
• 75104-08-4 2,6-dibenzoate of 1,3:4,5-di-O-(2-diethoxyphosphinylethylidene)galactitol 
• 591235-28-8 diethoxyphosphorylacetaldehyde tosylhydrazone 
• 1616475-91-2 ethyl phenyl (2,2-diethoxyethyl)phosphonate 
• 1431862-17-7 diethyl [2,2-bis(2,4,5-trimethoxyphenyl)ethyl]phosphonate 
• 1369960-67-7 diethyl 2-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-[2-(benzyloxy)ethoxy]ethylphosphonate 
• 1369960-66-6 diethyl 2-[2-(benzyloxy)ethoxy]-2-[2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)]ethylphosphonate 
• 1369960-65-5 diethyl 2-(2-(benzyloxy)ethoxy)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)ethylphosphonate 
• 1369960-64-4 diethyl 2-[2-(benzyloxy)ethoxy]-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)ethylphosphonate 

Relevant academic research and scientific papers

Condensation of resorcinol with phosphorylated acetals, synthesis of calix[4]resorcinolarenes with phosphorus-containing alkyl fragments in the lower rim

The reaction of resorcinol with phosphorylated acetals leads to formation of calix[4]resorcinolarenes having phosphonate, phosphinate, or (phosphinothioyl)sulfanylmethyl fragments in the lower rim of the molecule. Pleiades Publishing, Inc., 2006.

Synthesis of calix[4]resorcinarenes, containing phosphoryl fragments at the lower rim of the molecule

Reaction of resorcinol with phosphorylated acetals or ethoxyvinylphosphonic acid esters in acidic media leads to calix[4]resorcinarenes, containing dialkoxyphosphoryl fragments at the lower rim of the molecule. When the alkyl substituent in alkoxy groups at phosphorus atom is not very long, a partial hydrolysis of the initially formed products takes place to give calixarenes with alkoxyhydroxyphosphoryl fragments.

Phosphonodifluoropyruvate is a mechanism-based inhibitor of phosphonopyruvate decarboxylase from Bacteroides fragilis

Bacteroides fragilis, a human pathogen, helps in the formation of intra-abdominal abscesses and is involved in 90% of anaerobic peritoneal infections. Phosphonopyruvate decarboxylase (PnPDC), a thiamin diphosphate (ThDP)-dependent enzyme, plays a key role in the formation of 2-aminoethylphosphonate, a component of the cell wall of B. fragilis. As such PnPDC is a possible target for therapeutic intervention in this, and other phosphonate producing organisms. However, the enzyme is of more general interest as it appears to be an evolutionary forerunner to the decarboxylase family of ThDP-dependent enzymes. To date, PnPDC has proved difficult to crystallize and no X-ray structures are available. In the past we have shown that ThDP-dependent enzymes will often crystallize if the cofactor has been irreversibly inactivated. To explore this possibility, and the utility of inhibitors of phosphonate biosynthesis as potential antibiotics, we synthesized phosphonodifluoropyruvate (PnDFP) as a prospective mechanism-based inhibitor of PnPDC. Here we provide evidence that PnDFP indeed inactivates the enzyme, that the inactivation is irreversible, and is accompanied by release of fluoride ion, i.e., PnDFP bears all the hallmarks of a mechanism-based inhibitor. Unfortunately, the enzyme remains refractive to crystallization.

Determination of the Absolute Configuration of (?)-Hydroxynitrilaphos and Related Biosynthetic Questions

The ongoing search for bioactive natural products has led to the development of new genome-based screening approaches to identify possible phosphonate producing microorganisms. From the identified phosphonate producers, several until now unknown phosphonic acid natural products were isolated, including (hydroxy)nitrilaphos (4 and 5) and (hydroxy)phosphonocystoximate (7 and 6). We present the synthesis of phosphonocystoximate via an aldoxime intermediate. Chlorination and coupling with methyl N-acetylcysteinate furnished 6 after global deprotection. The obtained experimental data confirm the previously assigned structure of the natural product. We were also able to determine the absolute configuration of (?)-hydroxynitrilaphos. Chiral resolution of diethyl cyanohydroxymethylphosphonate (24) with Noe's lactol furnished both enantiomers of 4. Conversion of (+)-24 to (R)-2-amino-1-hydroxyethylphosphonic acid by reduction of the cyano-group showed (?)-hydroxynitrilaphos ultimately to be S-configured. Further, we present a 13C-isotope labeling strategy for 4 and 5 that will possibly solve the question of whether hydroxynitrilaphos is a biosynthetic intermediate or a downstream product of hydroxyphosphonocystoximate biosynthesis.

Synthesis of a new family of acyclic nucleoside phosphonates, analogues of TPases transition states

A 6-step procedure was developed for the synthesis of a new family of acyclic nucleoside phosphonates (ANPs), "PHEEPA" [(2-pyrimidinyl-2-(2- hydroxyethoxy)ethyl)phosphonic acids] in overall yields ranging from 4.5% to 32%. These compounds, which possess on one side a hydroxy function and on the other side a phosphonate group, can be considered either as potential antiviral agents or as transition state analogues of nucleoside phosphorylases such as thymidine phosphorylase.

Novel 1β-methylcarbapenems with isoxazoloethenyl moieties containing carboxylic acid sodium salt

The synthesis of novel 1β-methylcarbapenems 1a,b having sodium 5-(3- and 5-carboxylic acid)isoxazoloethenyl moieties at C-5 position of pyrrolidine ring and their biological evaluation are described. Both compounds showed potent and well-balanced antibacterial activity as well as high stability to DHP-I. The selected sodium 3-carboxylic acid derivative 1a possessed excellent DHP-I stability and advanced pharmacokinetic parameters in comparison with 2 and meropenem. The synthesis of novel 1β-methylcarbapenems 1a,b having sodium 5-(3- and 5-carboxylic acid)isoxazoloethenyl moieties at C-5 position of pyrrolidine ring and their biological evaluation are described. Both compounds showed potent and well-balanced antibacterial activity as well as high stability to DHP-I. The selected sodium 3-carboxylic acid derivative 1a possessed excellent DHP-I stability and advanced pharmacokinetic parameters in comparison with 2 and meropenem.

Synthesis and biological evaluation of cycloalkylidene carboxylic acids as novel effectors of Ras/Raf interaction

The protooncogenes Ras and Raf play important roles in signal transduction pathways regulated by mitogen-activated protein kinases. Mutations of Ras that arrest the protein in its active state are frequently implicated in tumor formation. We used Ras and Raf proteins in the yeast two-hybrid system to search for natural or synthesized substances capable of modulating Ras/Raf interaction by specifically binding to one of the interacting partners. We found that cycloalkylidene carboxylic acids enhanced Ras/Raf interaction by acting on the cysteine-rich domain of Raf. Several analogues of the active substance 2-cyclohexylidene propanoic acid were synthesized and the importance of the semicyclic double bond in the stabilization of Ras/Raf interaction was demonstrated. Variation of the size and the substituents of the cyclic system as well as the length of the carboxylic acid resulted in enhanced Ras/Raf interaction.

Synthesis and Synthetic Utilization of α-Functionalized Vinylphosphonates Bearing β-Oxy or β-Thio Substituents

The β-hetero-substituted vinylphosphonates la-c on treatment with LDA or LTMP were readily lithiated at the α-position of the phosphono group, and the resulting α-lithiovinylphosphonates were trapped with various electrophiles to afford the corresponding α-functionalized vinylphosphonates 2-14 in 55-96% yields. The Friedel-Crafts reaction of α-(silyl)- or a-(germyl)-phosphonoketene dithioacetals 2, 9, or 4 with acid chlorides gave α-acylated phosphonoketene dithioacetals 15-19 in 53-91% yields. The palladium-catalyzed cross-coupling reaction of β-ethoxy-α-(tributylstannyl)vinylphosphonate 13 with a variety of organic halides (R = acyl, allyl, aryl, etc.) provided β-ethoxy-α-substituted vinylphosphonates 21-26 in good to moderate yields. The palladium-mediated cross-coupling reaction of α-(iodo)vinylphosphonates 7 and 14 with terminal acetylenes afforded α-alkynylated vinylphosphonates 41-44 in 69-83% yields. Several α-functionalized β-hetero-substituted vinylphosphonates were applied to the synthesis of pyrazoles and an isoxazole possessing a phosphono function.

Water soluble phosphorylated polysiloxanes

This invention relates to a novel family of phosphorylated polysiloxanes which are non-ionic and water soluble. When these polysiloxanes are dissolved in water, the resulting solutions exhibit low surface tensions. The invention also relates to phosphorylated polysiloxanes which are gels or hydrogels. The invention further contemplates methods of synthesizing the phosphorylated polysiloxanes.