15916-48-0

Usage

Uses

Used in Pharmaceutical Industry:
DIETHYL-3-BUTENYLPHOSPHONATE 95 is used as a reactant for the synthesis of various pharmaceutical compounds, such as:
1. Antiviral C-5-substituted pyrimidine acyclic nucleoside phosphonates, which are selected as human thymidylate kinase substrates. These compounds have potential applications in the treatment of viral infections.
2. Antimalarial agents through the halogenation of di-Et butenylphosphonate. This process leads to the development of new antimalarial drugs that can help combat the growing resistance to existing treatments.
Used in Chemical Synthesis:
DIETHYL-3-BUTENYLPHOSPHONATE 95 is used as a reactant in the synthesis of various organic compounds, including:
1. Bicyclo[3.3.1]alkenone framework compounds by gold-catalyzed Diels-Alder reactions. These compounds have potential applications in the development of new pharmaceuticals and agrochemicals.
2. Bisphosphonate enynes, which are versatile building blocks in organic synthesis and can be used to construct complex molecular structures.
3. Phosphic derivatives of carbohydrates through chemoenzymatic synthesis. These derivatives have potential applications in the development of new drugs and bioactive compounds.
Used in Catalyst Development:
DIETHYL-3-BUTENYLPHOSPHONATE 95 is used as a reactant for the development of new catalysts in:
1. Remote supramolecular control of catalyst selectivity in hydroformylation of alkenes. This process can lead to the development of more efficient and selective catalysts for industrial applications.
2. Intermolecular metal-catalyzed carbenoid cyclopropanations. This reaction can be used to synthesize various cyclopropane-containing compounds, which are important building blocks in the pharmaceutical and agrochemical industries.

InChI:InChI=1/C8H17O3P/c1-4-7-8-12(9,10-5-2)11-6-3/h4H,1,5-8H2,2-3H3

Upstream product

• 683-08-9 Diethyl methylphosphonate 
• 106-95-6 allyl bromide 
• 110625-05-3 diethyl-1-magnesium chloride methanephosphonate 
• 5162-44-7 1-bromo-4-butene 
• 762-04-9 phosphonic acid diethyl ester 
• 122-52-1 triethyl phosphite 
• 762-04-9 Diethyl phosphonate 
• 10419-77-9 diethyl iodomethanephosphonate 
• 24850-33-7 allyltributylstanane 
• 121-45-9 phosphorous acid trimethyl ester 

Downstream Products

• 1028279-25-5 [1-(Hydroxy-diphenyl-methyl)-but-3-enyl]-phosphonic acid diethyl ester 
• 3986-95-6 diethyl (3-oxopropyl)phosphonate 
• 174538-49-9 {4-[5-(3-Benzoyl-thioureido)-4-carbamoyl-[1,2,3]triazol-1-yl]-butyl}-phosphonic acid diethyl ester 
• 174538-52-4 {4-[5-(3-Benzoyl-2-methyl-isothioureido)-4-carbamoyl-[1,2,3]triazol-1-yl]-butyl}-phosphonic acid diethyl ester 
• 174538-64-8 {4-[5-(3-Benzoyl-thioureido)-4-carbamoyl-[1,2,3]triazol-1-ylmethoxy]-butyl}-phosphonic acid diethyl ester 
• 174538-67-1 {4-[5-(3-Benzoyl-2-methyl-isothioureido)-4-carbamoyl-[1,2,3]triazol-1-ylmethoxy]-butyl}-phosphonic acid diethyl ester 
• 98732-85-5 (E)-2-(diethoxyphosphinyl)-3-phenylprop-2-enyl methyl ketone 
• 1027313-00-3 (5-Iodomethyl-2-phenyl-tetrahydro-furan-3-yl)-phosphonic acid diethyl ester 
• 1026728-33-5 (5-Iodomethyl-2,2-diphenyl-tetrahydro-furan-3-yl)-phosphonic acid diethyl ester 
• 1266603-67-1 C₉H₁₉O₄P 
• 166528-15-0 C₉H₁₉O₄P 

Relevant academic research and scientific papers

Amino acid based prodrugs of a fosmidomycin surrogate as antimalarial and antitubercular agents

Fosmidomycin is a natural antibiotic with promising IspC (DXR, 1-deoxy-D-xylulose-5-phosphate reductoisomerase) inhibitory activity. This enzyme catalyzes the first committed step of the non-mevalonate isoprenoid biosynthesis pathway, which is essential i

Chemoselective Activation of Diethyl Phosphonates: Modular Synthesis of Biologically Relevant Phosphonylated Scaffolds

Phosphonates have garnered considerable attention for years owing to both their singular biological properties and their synthetic potential. State-of-the-art methods for the preparation of mixed phosphonates, phosphonamidates, phosphonothioates, and phos

Phosphonodiamidate prodrugs of N-alkoxy analogs of a fosmidomycin surrogate as antimalarial and antitubercular agents

A series of N-alkoxy analogs of a L-leucine ethyl ester phosphonodiamidate prodrug of a fosmidomycin surrogate were synthesized and investigated for their ability to inhibit in vitro growth of P. falciparum and M. tuberculosis. These compounds originate b

In-chain poly(phosphonate)s via acyclic diene metathesis polycondensation

In-chain poly(phosphonate)s have been prepared via acyclic diene metathesis polymerization of three different monomers. Novel unsaturated phosphonate monomers with asymmetric structure have been developed. The monomers are accessible via a three-step synthesis that can be easily scaled up. This is the first report on poly(phosphonate)s by olefin metathesis where the stable carbon-phosphorus linkage is localized in the polymer backbone. This changes the nature of the degradation products compared to other poly(phosphoester)s. Polymers with molecular weights up to 31000 g mol-1 can be achieved and have been characterized in detail NMR spectroscopy, size exclusion chromatography, thermogravimetry, and differential scanning calorimetry. They have been also compared to structural analogues polyphosphates with respect to crystallization (SAXS, WAXS) and their rheological behavior. Also, solution grown crystals were analyzed rendering some of the herein reported poly(phosphonate)s as interesting defect poly(ethylene)-like structures.

Ene-Yne Metathesis of Allylphosphonates and Allylphosphates: Synthesis of Phosphorus-Containing 1,3-Dienes

A variety of ene-yne cross metathesis reactions were performed using unsaturated phosphonate and phosphate reagents, affording the corresponding phosphorylated 1,3-diene products in good to excellent yields. These difficult ene-yne metatheses employed a Grubbs catalyst bearing a cyclic amino alkyl carbene ligand. A variety of terminal alkynes of varying substitution underwent the reaction, and different phosphorus-containing alkenes were found to give the conjugated diene products in high yields. The resulting dienes were further transformed by Horner-type Wittig reactions and a Diels-Alder cycloaddition.

Indium(III) halide-catalyzed UV-irradiated radical coupling of iodomethylphosphorus compounds with various organostannanes

The first catalytic radical coupling of iodomethylphosphorus compounds was accomplished with allyl-, alkenyl-, and allenylstannanes under UV irradiation in the presence of an indium(III) halide catalyst, for which a transmetalated allylic indium species was confirmed to be an active radical species.

Hydroboration of unsaturated phosphonic esters: Synthesis of boronophosphonates and trisubstituted vinylphosphonates

equation presented Hydroboration of vinyl phosphonates with pinacolborane (PBH) proceeds to give phosphonoboronates, 2. Surprisingly, such compounds have not been reported before. The reaction works well with terminal alkenylphosphonates. Internal alkenylphosphonates give complex mixtures. Hydroboration/Suzuki coupling of alkynylphosphonates, with PBH, in a one-pot procedure gives trisubstituted vinylphosphonates in good overall yields and provides a new synthesis of these compounds.

The stereoselective synthesis of cyclopropylphosphonate analogs of nucleotides

1-Alkenylphosphonic acid derivatives of purines have been proven to exhibit significant antiviral activity among these series of compounds. Here we disclose the stereoselective synthesis of the constrained analogs of 1-alkenylphosphonate derivatives of purines via intramolecular epoxide opening reaction of γ,δ-epoxyalkanephosphonates with subsequent Mitsunobu coupling reactions with purine bases.

Guanine, pyrazolo[3,4-d]pyrimidine, and triazolo[4,5-d]pyrimidine (8-azaguanine) phosphonate acyclic derivatives as inhibitors of purine nucleoside phosphorylase

Phosphonate acyclic derivatives of guanines, pyrazolo[3,4-d]pyrimidines, and triazolo[4,5-d]-pyrimidines (8-azaguanines) are inhibitors of the enzyme purine nucleoside phosphorylase (PNPase) with K′1 values ranging from 0.05 to 1.6 μM. These compounds are enzymatically stable congeners of the potent PNPase inhibitor acyclovir diphosphate (53).

PREPARATION OF TETRAETHYL BUT-3-ENYLIDENE-1,1-BISPHOSPHONATE AND STUDY OF ITS REACTIVITY AS A SYNTHON OF TETRAETHYL 3,4-DIAMINOBUTYLIDENE-1,1-BISPHOSPHONATE

We decribe a new preparation of tetraethyl but-3-enylidene-1,1-bisphosphonate 7.This preparation requires the phosphonylation of diethyl but-3-enyl-1-phosphonate which is obtained by the Michaelis-Becker reaction.Various methods of vic-diamination are studied to obtain tetraethyl 3,4-diaminobutylidene-1,1-bisphosphonate 11.The best approach consists in preparing the diazide by action of sodium azide, in the presence of manganese (III) acetate, and by reducing it in solution in tetrahydrofuran by triphenylphosphine in the presence of water.Hydrolysis by concentrated hydrochloric acid produces 3,4-diaminobutylidene-1,1-bisphosphonic acid 3.Key words: gem-Bisphosphonates; vic-diamine; 3,4-diaminobutylidene-1,1-bisphosphonates: synthesis of