80792-13-8

Basic information

• Product Name: TOLUENE-4-SULFONIC ACID DIMETHOXY-PHOSPHORYLMETHYL ESTER
• Synonyms: TOLUENE-4-SULFONIC ACID DIMETHOXY-PHOSPHORYLMETHYL ESTER
• CAS NO: 80792-13-8
• Molecular Formula: C₁₀H₁₅O₆PS
• Molecular Weight: 294.26
• Mol File: 80792-13-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: TOLUENE-4-SULFONIC ACID DIMETHOXY-PHOSPHORYLMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: TOLUENE-4-SULFONIC ACID DIMETHOXY-PHOSPHORYLMETHYL ESTER(80792-13-8)
• EPA Substance Registry System: TOLUENE-4-SULFONIC ACID DIMETHOXY-PHOSPHORYLMETHYL ESTER(80792-13-8)

Safety Data

• Hazardous Substances Data: 80792-13-8(Hazardous Substances Data)

Upstream product

• 24630-67-9 hydroxymethyl-phosphonic acid dimethyl ester 
• 98-59-9 p-toluenesulfonyl chloride 
• 104-15-4 toluene-4-sulfonic acid 
• 27491-70-9 dimethyl diazomethylphosphonate 

Downstream Products

• 1201795-29-0 methyl tosyloxymethanephosphonate 
• 854389-42-7 methyl (5'-O-dimethoxytrityl-3'-O-thymidinyl)methylphosphonate 
• 854389-60-9 [(2R,3S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxymethyl]-phosphonic acid monomethyl ester 
• 854389-55-2 [(2R,3R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxymethyl]-phosphonic acid monomethyl ester 
• 854389-48-3 [(2R,3R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxymethyl]-phosphonic acid monomethyl ester 
• 854389-39-2 [(2R,3S,5R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxymethyl]-phosphonic acid monomethyl ester 

Relevant articles and documents

Methyl 4-toluenesulfonyloxymethylphosphonate, a new and versatile reagent for the convenient synthesis of phosphonate-containing compounds

A straightforward procedure leading to the new phosphonylating reagent, methyl 4-toluenesulfonyloxymethylphosphonate, requiring no chromatographic purification is described. This stable reagent works with the same efficiency as dimethyl and other dialkyl esters for the introduction of an O-phosphonomethyl moiety while, in contrast to dimethyl ester, it does not cause any unwanted methylation of sensitive functionalities. Its utility for the alkylation of protected nucleosides in high yield is exemplified.

PREPARATION OF 5'-O-PHOSPHONYLMETHYL ANALOGUES OF NUCLEOSIDE-5'-PHOSPHATES, 5'-DIPHOSPHATES AND 5'-TRIPHOSPHATES

Reaction of a trialkyl phosphite (VI) or sodium salt of dialkyl phosphite (V) with bromomethyl acetate afforded dialkyl acetoxymethanephosphonates VII which were alcoholyzed to dialkyl hydroxymethanephosphonates VIII.Tosylation of the compounds VIII gave dialkyl p-toluenesulfonyloxymethanephosphonates IX which on reaction with 2',3'-O-isopropylideneribonucleosides (I), 2',3'-O-ethoxymethyleneribonucleosides (XI) or 3'-O-tetrahydropyranyl-2'-deoxyribonucleosides in the presence of sodium hydride, followed by acid hydrolysis, were converted into alkyl esters of 5'-O-phosphonylmethylnucleosides XII.Treatment of compounds XII with trimethylsilyl iodide led to 5'-O-phosphonylmethylnucleosides II and XIV.The ribo derivatives II were also obtained in low yields by reaction of compounds I with sodium chloromethanephosphonate in the presence of sodium hydride.Compound II reacted with morpholine in the presence of N,N'-dicyclohexylcarbodiimide to give morpholides XV which on treatment with phosphate afforded 5'-O-phosphorylphosphonylmethylribonucleosides XVI.Analogously, 5'-O-diphosphorylphosphonylmethylribonucleosides XVII were obtained from the derivatives XV by reaction with diphosphate.The compounds II are resistant towards E. coli alkaline phosphomonoesterase and snake venom and bull semen 5'-nucleotidase.E. coli alkaline phosphomonoesterase degrades the compounds XVI and XVII to compounds II and inorganic phosphate.