65600-74-0

Usage

Uses

Used in Chemical Warfare:
ETHYL (DIETHOXYMETHYL)PHOSPHINATE is used as a chemical warfare agent for its highly toxic properties and ability to cause severe and often lethal effects on the human nervous system. Its rapid absorption through various routes and potent inhibition of the enzyme acetylcholinesterase make it a dangerous weapon in the context of warfare.

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 6303-21-5 hypophosphorous acid 

Downstream Products

• 134150-78-0 1-Benzhydryl-3-(diethoxymethyl-O-ethylphosphinyl)azetidine 
• 164531-84-4 ethyl diethoxymethyl(3-nitrophenyl)phosphinate 
• 164531-83-3 ethyl diethoxymethyl(4-nitrophenyl)phosphinate 
• 23587-54-4 ethyl diethoxymethyl(phenyl)phosphonate 
• 227959-44-6 3-(diethoxymethyl-ethoxy-phosphinoyl)-3-hydroxy-piperidine-1-carboxylic acid benzyl ester 
• 886990-15-4 diethoxymethyl-{[1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-cyclohexyl]-hydroxy-methyl}-phosphinic acid ethyl ester 
• 1096144-04-5 4,5-bis-benzyloxy-6-benzyloxymethyl-2-diethoxymethyl-2-oxo-2λ5-[1,2]oxaphosphinan-3-ol 
• 1096143-77-9 4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-2-oxo-2-diethoxymethyl-tetrahydro-6λ*5*-[1,3]dioxolo[4,5-d][1,2]oxaphosphinan-3-aminophenyl 
• 1096143-79-1 4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-2-oxo-2-diethoxymethyl-tetrahydro-6λ*5*-[1,3]dioxolo[4,5-d][1,2]oxaphosphinan-3-aminotoluyl 
• 344413-71-4 ethyl 3-[(diethoxymethyl)(ethoxy)phosphoryl]-2-fluoropropanoate 
• 1058227-17-0 ethyl diethoxymethyl-(S_S,R_C,R_P)-(+)-(1-(tert-butylsulfinylamino)-(1-phenylethyl))phosphinate 
• 1058227-35-2 ethyl diethoxymethyl-(S_S,R_C,S_P)-(+)-(1-(tert-butylsulfinylamino)-(1-phenylethyl))phosphinate 
• 1058227-26-1 ethyl diethoxymethyl-(S_S,R_C,R_P)-(+)-(1-(tert-butylsulfinylamino)-(1-(p-bromophenyl)ethyl))phosphinate 
• 1058227-44-3 ethyl diethoxymethyl-(S_S,R_C,S_P)-(+)-(1-(tert-butylsulfinylamino)-(1-(p-bromophenyl)ethyl))phosphinate 

Relevant academic research and scientific papers

Synthesis of potential inhibitors of the enzyme pantothenate synthetase

Three phosphinate salts (5), (6) and (7) were prepared as potential inhibitors of the enzyme pantothenate synthetase. The synthesis of compound (5) utilises a (diethoxymethyl)-protected phosphinate (8) as a new reagent for the formation of unsymmetrical phosphinic acids and esters. Initial P-alkylation of (8) followed by a selective deprotection sequence yields intermediate P-H phosphinates (16) and (21) which can be P-alkylated a second time. Enzyme assays have been performed with the target compound and the results are discussed.

Synthesis of unnatural 2- and 3-deoxyfuranose analogues

This Letter describes the synthesis of two racemic analogues of unnatural 3′-deoxy and 2′-deoxy sugars, where a phosphorus atom replaces the carbon atom in the 2′- or 3′-position. Two methods of four- and 5-steps were developed affording these new unnatur

Rapid and efficient synthesis of unsymmetrical phosphinic acids r′t(o)ohr″

A new synthesis of unsymmetrical phosphinic acids R′P(O)OHR″ has been evaluated, The first P-C bond was formed by base-promoted H-phosphinate alkylation of a protected H-phosphinate, which is easier and safer to handle, A onepot methodology was developed for the second P-C bond formation reaction that: involves the sila-Arbuzov reaction. This methodology was then extended to the synthesis of a dialkylphosphinic acid with an amino functionality.

NEW PHOSPHORUS CONTAINING HETEROCYCLIC COMPOUNDS, SUGAR ANALOGUES, AND COMPOSITIONS HAVING ANTI-CANCER ACTIVITY CONTAINING THE SAME

The invention provides new anticancer compounds of formula (1) such as defined in the present description. The invention also provides pharmaceutical compositions to be used in human or veterinary medicine, comprising at least one compound of formula (1). The present invention further relates to a compound of formula (1) such as defined in the present description, for use as a drug. The invention further relates to the use of a compound of formula (1) for manufacturing a human or animal anticancer pharmaceutical composition.

Synthesis of P,N-heterocycles from ω-amino-H-phosphinates: Conformationally restricted α-amino acid analogs

(Chemical Equation Presented) P,N-Heterocycles (3-hydroxy-1,3- azaphospholane and 3-hydroxy-1,3-azaphosphorinane-3-oxide) are synthesized in moderate yield from readily available ω-amino-H-phosphinates and aldehydes or ketones via an intramolecular Kabachnik-Fields reaction. The products are conformationally restricted phosphinic analogs of α-amino acids. The multigram-scale syntheses of the H2N(CH2) nPO2H2 phosphinic precursors (n = 1, 2, 3) and some derivatives are also described.

A concise and first synthesis of α-aminophosphinates with two stereogenic atoms leading to optically pure α-amino-H-phosphinic acids

A highly stereoselective synthesis of ω-aminophosphinates by nucleophilic attack of ethyl diethoxymethylphosphinate to Ellman's N-(tert-butanesulfinyl) ketimines by using Rb2CO3 as a base at room temperature was reported. In the first set of experiments, (S)-(tert-butane-sulfinyl)methyl (p-bromo)phenylketimine (1j) was used as the model compound to study its reaction with ethyl diethoxymethyl-phosphinate. Ethyl diethoxymethyiphosphinate and Rb2CO3 in CH 2Cl2 were placed in a 20 ml, Schienk flask and (5)-N-tert-butanesulfinylketimines 1 were then added at room temperature. The mixture was then stirred for 3-4 d, while being carefully monitored by TLC. The H NMR analysis showed that they have minor differences with shifts at 3.5 and 4.2 ppm, which can be assigned to the diethoxymethyl and the ethoxyl groups of the products.

Synthesis of bispyrrolidines by radical cyclisation of diallylamines using phosphorus hydrides

Sequential radical addition-cyclisation reactions of diallylamines using either hypophosphorous acid or a bisphosphinothioate are shown to afford bispyrrolidines in good to excellent yields. Georg Thieme Verlag Stuttgart.

PROCESS FOR PREPARATION OF ALKYL PHOSPHINATES

The invention relates to a new process for the production of alkyl dialkoxyalkylphosphinates. A hypophosphite salt is used in the process.

Preparation of phosphinodipeptide analogs as building blocks for pseudopeptides synthesis

A simple and effective preparation of phosphinodipeptides, in good overall yields, has been developed. This one pot procedure, allowing the variation of the substituents in α and/or β position to the phosphorus atom and also in α position to the nitrogen atom, consists in the addition of alkyl hypophosphites to imines, followed by Michael-addition on acrylates. To show the value of phosphinodipeptides analogs 1 as synthetic intermediates, selective deprotections of the three functional groups are described.

Syntheses and GABA receptor binding properties of 4-amino-1-, 2-, and 3- hydroxybutylphosphinic acids

Novel racemic 4-amino-1-, 2-, and 3-hydroxybutylphosphinic acids and the corresponding 4-amino-1-, 2-, and 3-hydroxybutyl methylphosphinic acids have been synthesized. The phosphinic acid groups are bioisosteres of the carboxylic acid group, and some of these hydroxy amino acids are GABA(B) antagonists. The novel phosphinic acids were evaluated for their GABA(A) and GABA(B) receptor binding properties using rat brain synaptosomes and were also tested for GABAergic activity in a guinea pig ileum model. None of the phosphinic acids tested were found to be active.