35717-98-7

Basic information

• Product Name: (DIISOPROPOXYPHOSPHORYL)METHYL 4-METHYLBENZENESULFONATE
• Synonyms: (DIISOPROPOXYPHOSPHORYL)METHYL 4-METHYLBENZENESULFONATE;[[[(4-Methylphenyl)sulfonyl]oxy]methyl]phosphonic acid bis(isopropyl) ester;Diisopropyl [(p-tolylsulfonyl)oxy]methanephosphonate;(Diisopropoxyphosphoryl)Methyl 4-Methylbenzenesulfonate [[[(4-Methylphenyl)sulfonyl]oxy]Methyl]phosphonic acid;bis(isopropyl) ester
• CAS NO: 35717-98-7
• Molecular Formula: C₁₄H₂₃O₆PS
• Molecular Weight: 350.37
• Mol File: 35717-98-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 454.3±28.0 °C(Predicted)
• Appearance: /
• Density: 1.206
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (DIISOPROPOXYPHOSPHORYL)METHYL 4-METHYLBENZENESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: (DIISOPROPOXYPHOSPHORYL)METHYL 4-METHYLBENZENESULFONATE(35717-98-7)
• EPA Substance Registry System: (DIISOPROPOXYPHOSPHORYL)METHYL 4-METHYLBENZENESULFONATE(35717-98-7)

Safety Data

• Hazardous Substances Data: 35717-98-7(Hazardous Substances Data)

Usage

General Description

The chemical "(DIISOPROPOXYPHOSPHORYL)METHYL 4-METHYLBENZENESULFONATE" is a phosphoramidate compound consisting of a methyl ester of 4-methylbenzenesulfonic acid and diisopropoxyphosphoryl group. It is commonly used as a coupling reagent in peptide and protein synthesis, as well as in the preparation of phosphoramidate prodrugs. (DIISOPROPOXYPHOSPHORYL)METHYL 4-METHYLBENZENESULFONATE is often utilized as a stabilizing agent for drugs susceptible to hydrolysis, as well as in the synthesis of various pharmaceuticals and bioactive compounds. Its unique chemical structure makes it an important intermediate in organic synthesis and medicinal chemistry.

Upstream product

• 691-96-3 diisopropyl phosphite 
• 98-59-9 p-toluenesulfonyl chloride 
• 1809-20-7 diisopropyl hydrogenphosphonate 
• 24630-68-0 diisopropyl hydroxymethylphosphonate 

Downstream Products

• 138247-57-1 (S)-1-O-benzyl-2-O-<(diisopropylphosphono)methyl>-1,2-propanediol 
• 173277-58-2 (R)-1-(benzyloxy)propan-2-yl 4-methylbenzenesulfonate 
• 627510-49-0 [(R)-2-(6-Benzoylamino-purin-9-yl)-1-methyl-ethoxymethyl]-phosphonic acid diisopropyl ester 
• 160616-48-8 [(R)-2-(2-Benzoylamino-6-oxo-1,6-dihydro-purin-9-yl)-1-methyl-ethoxymethyl]-phosphonic acid diisopropyl ester 
• 903882-64-4 diisopropyl [1-(6-N-benzoyladenin-9-yl)-β-D-xylofuranos-2-O-yl]methylphosphonate 
• 903882-65-5 diisopropyl [3-O-benzoyl-1-(6-N-benzoyladenin-9-yl)-5-O-(4,4'-dimethoxytrityl)-β-D-xylofuranos-2-O-yl]methylphosphonate 
• 903882-56-4 diisopropyl [1-(6-N-benzoyladenin-9-yl)-β-D-ribofuranos-2-O-yl]methylphosphonate 
• 903882-60-0 diisopropyl [1-(6-N-benzoyladenin-9-yl)-β-D-arabinofuranos-2-O-yl]methylphosphonate 
• 903882-61-1 diisopropyl [3-O-benzoyl-1-(6-N-benzoyladenin-9-yl)-5-O-(4,4'-dimethoxytrityl)-β-D-arabinofuranos-2-O-yl]methylphosphonate 
• 903882-57-5 diisopropyl [3-O-benzoyl-1-(6-N-benzoyladenin-9-yl)-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranos-2-O-yl]methylphosphonate 

Relevant articles and documents

THYROID HORMONE RECEPTOR AGONIST AND USE THEREOF

A thyroid hormone receptor agonist and its use in the treatment of a disease associated thyroid hormone receptor beta are described. The compound can be effective in lowering cholesterol with minimum or no adverse effects on the heart or thyroid hormone axis.

Synthesis of cyclopropane-containing phosphorus compounds by radical coupling of butenylindium with iodo phosphorus compounds

The radical coupling of α- or β-iodo phosphorus compounds such as iodo phosphonate, iodo phosphane oxide, and iodo phosphonothioate with butenylindium species, prepared by transmetalation between a (cyclopropylmethyl)stannane and InBr3, afforded the corresponding cyclopropylmethylated products. The radical reaction was initiated by the radical species generated from butenylindium assisted by a small amount of oxygen. Butenylindium works not only as a cyclopropylmethylating reagent, but also as a radical initiator. For successful coupling, a tin/indium transmetalation was used, where it was important for the tin halide by-product to be inert to the reaction system. In addition, the transmetalation of a (cyclopropylmethyl)stannane and InBr3 provided the dibutenylindium bromide as a single product, which smoothly coupled with the unstable phosphonyl radical species from the iodo phosphorus compound. A photochemical method (UV irradiation) was also applied and accelerated the coupling reaction. The cyclopropylmethylated phosphonate produced was a good intermediate in the Horner-Wadsworth-Emmons reaction and gave functionalized olefins bearing the cyclopropane moiety. Copyright

9-[(Phosphonoalkyl)benzyl]guanines. Multisubstrate analogue inhibitors of human erythrocyte purine nucleoside phosphorylase

A series of 9-[(phosphonoalkyl)benzyl]guanines was synthesized and tested for inhibition of human erythrocyte purine nucleoside phosphorylase (PNPase). Inhibitors of PNPase should be T-cell selective, immunosuppressive agents with potential clinical utili