115142-03-5

Basic information

• Product Name: Phosphoric acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester 3-nitro-phenyl ester
• Synonyms: Phosphoric acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester 3-nitro-phenyl ester
• CAS NO: 115142-03-5
• Molecular Weight: 445.279
• Mol File: 115142-03-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Phosphoric acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester 3-nitro-phenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphoric acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester 3-nitro-phenyl ester(115142-03-5)
• EPA Substance Registry System: Phosphoric acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester 3-nitro-phenyl ester(115142-03-5)

Safety Data

• Hazardous Substances Data: 115142-03-5(Hazardous Substances Data)

Upstream product

• 554-84-7 meta-nitrophenol 
• 38319-29-8 m-nitrophenyl phosphorodichloridate 
• 115142-13-7 Phosphoric acid (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tetrahydro-pyran-2-yloxy)-2-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester 3-nitro-phenyl ester 

Downstream Products

• 554-84-7 meta-nitrophenol 
• 606-02-0 uridine 2',3'-cyclic phosphate 

Relevant articles and documents

Charge Description of Base-Catalyzed Alcoholysis of Aryl Phosphodiesters: A Ribonuclease Model

The release of substituted phenol from aryl uridine-3'-phosphates is catalyzed by bases and involves cyclization to form the 2',3'-cyclic nucleotide.The rate constants for imidazole and hydroxide ion catalysis (kim and kOH, respectively) obey the Broensted equations (25 deg C and 0.25 M ionic strength) log kim = -0.59 pKArOH + 1.40 (n = 7, r = 0.955) and log kOH = -0.54 pKArOH + 6.68 (n = 9, r = 0.967).General-base-catalyzed release of 4-nitrophenol from the 4-nitrophenyl ester (kB) obeys the Broensted relationship log kB = 0.67 pKBH - 7.50 (n = 7, r = 0.989).Charge changes on base and leaving group atoms as determined from the corresponding β and βeq values do not balance.Comparison with data in the literature indicates that the difference in charge may be assigned to the attacking oxygen (2'-hydroxyl) rather than to the phosphoryl oxygens in the O...PO2... group of atoms.Both P-O bond forming and bond fission components of the reaction are considered to be only weakly advanced in a transition state that lies on a concerted pathway.