116384-58-8

Basic information

• Product Name: Phosphonic acid, [[2-[[(4-methylphenyl)sulfonyl]oxy]ethoxy]methyl]-, diethyl ester
• Synonyms: .diethyl 2-(phosphonomethoxy)ethyl p-toluene sulfonate;.diethyl p-toluenesulfonyloxyethoxymethanephosphonate;.Diethyl 2-p-toluenesulfonyloxyethoxymethylphosphonate;Diethyl 2-p-Toluenesulfonyloxyethoxymethanephosphonate
• CAS NO: 116384-58-8
• Molecular Formula: C14H23O7PS
• Molecular Weight: 366.372
• Mol File: 116384-58-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Phosphonic acid, [[2-[[(4-methylphenyl)sulfonyl]oxy]ethoxy]methyl]-, diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonic acid, [[2-[[(4-methylphenyl)sulfonyl]oxy]ethoxy]methyl]-, diethyl ester(116384-58-8)
• EPA Substance Registry System: Phosphonic acid, [[2-[[(4-methylphenyl)sulfonyl]oxy]ethoxy]methyl]-, diethyl ester(116384-58-8)

Safety Data

• Hazardous Substances Data: 116384-58-8(Hazardous Substances Data)

Upstream product

• 100708-15-4 2-((diethoxyphosphoryl)methoxy)ethyl acetate 
• 98-59-9 p-toluenesulfonyl chloride 
• 116384-55-5 diethyl 2-hydroxyethoxymethanephosphonate 

Downstream Products

• 1082741-32-9 C₂₄H₃₇N₆O₅P 
• 1252577-04-0 {2-[6-amino-2-(4-hexyl-3-hydroxyphenylamino)-purine-9-yl]-ethoxymethyl}-phosphonic acid diethyl ester 
• 1082741-23-8 {2-[6-amino-2-(4-butyl-3-hydroxy-phenylamino)-purin-9-yl]-ethoxymethyl}-phosphonic acid diethyl ester 
• 1252577-12-0 {2-[6-chloro-2-(4-butyl-3-hydroxyphenylamino)-purin-9-yl]-ethoxymethyl}-phosphonic acid diethyl ester 
• 1252577-11-9 {2-[6-chloro-2-(4-hexyl-3-hydroxyphenylamino)-purin-9-yl]-ethoxymethyl}-phosphonic acid diethyl ester 
• 1252577-10-8 (2-{2-[3-(tert-butyldiphenylsiloxy)-4-butyl-phenylamino]-6-chloro-purin-9-yl}-ethoxymethyl)-phosphonic acid diethyl ester 
• 1252577-09-5 (2-{2-[3-(tert-butyldiphenylsiloxy)-4-hexylphenylamino]-6-chloro-purin-9-yl}-ethoxymethyl)-phosphonic acid diethyl ester 
• 116384-54-4 Ethyl Ester of 9-(2-Phosphonylmethoxyethyl)adenine 
• 116384-53-3 [[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester 
• 117087-39-5 1-[2-(Phosphonomethoxy)ethyl]cytosine 

Relevant articles and documents

Antitumor effects of guanosine-analog phosphonates identified by molecular modelling

Aiming to address new drug targets, molecular modelling is gaining increasing importance although the prediction capability of the in silico method is still under debate. For an improved treatment of actinic keratosis and squamous cell carcinoma, inhibitors of human DNA polymerase α (pol α) are developed by docking nucleoside phosphonate diphosphates into the active site of pol α. The most promising prodrugs OxBu and OxHex were then prepared by total synthesis and tested in the squamous cancer cell line SCC25. OxBu and OxHex proved cytotoxic and antiproliferative in the nanomolar concentration range and thus exceeded activity of aphidicolin, the relevant model compound, and 5-fluorouracil, the current standard for the therapy of actinic keratosis. Interestingly, the cytotoxicity in normal human keratinocytes with OxHex was clearly less pronounced and even not detectable with OxBu. Moreover, cytotoxicity of OxBu in particular with the colorectal carcinoma cell line HT29 even surmounted cytotoxicity in SCC25, and other tumor cell lines were influenced, too, by both agents. Taken together, OxBu and OxHex may offer a new approach to cancer therapy, given the agents are sufficiently well tolerated in vivo which is to be suspected beside their chemical structure.

SYNTHESIS OF 9-(2-PHOSPHONYLMETHOXYETHYL)ADENINE AND RELATED COMPOUNDS

Diethyl 2-hydroxyethoxymethanephosphonate (VIII) was converted into diethyl 2-halogenoethoxymethanephosphonates IXa and IXb by reaction with triphenylphosphine and tetrachloromethane or tetrabromomethane; analogous reaction of VIII with p-toluenesulfonyl chloride afforded diethyl 2-(p-toluenesulfonyloxy)ethoxymethanephosphonate (IXc).Reaction of sodium salt of adenine with compounds IX led to 9-(2-diethoxyphosphonylmethoxyethyl)adenine (X).Compound X was converted into 9-(2-phosphonylmethoxyethyl)adenine (II) by treatment with bromotrimethylsilane whereas alkaline hydrolysis of X gave ethyl ester Vb.Reaction of 9-(2-hydroxyethyl)adenine (IIIa) or its N6-benzoyl derivative IIIb with dimethyl p-toluenesulfonyloxymethanephosphonate (IV) in the presence of sodium hydride, followed by alkaline hydrolysis yielded methyl ester Va.Morpholide XI reacted with an inorganic phosphate and diphosphate to give 9-(2-phosphorylphosphonylmethoxyethyl)adenine (XII) and 2-(diphosphorylphosphonylmethoxyethyl)adenine (XIII), respectively.