114262-49-6

Basic information

• Product Name: 1-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione
• Synonyms: 1-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione;Sofosbuvir Impurity 12;Sofosbuvir metabolites GS331007;1-(2-C-Methyl-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione
• CAS NO: 114262-49-6
• Molecular Formula: C₁₀H₁₄N₂O₆
• Molecular Weight: 258.22796
• Mol File: 114262-49-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 132-135 °C
• Appearance: /
• Density: 1.572±0.06 g/cm3(Predicted)
• PKA: 9.39±0.10(Predicted)
• CAS DataBase Reference: 1-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione(114262-49-6)
• EPA Substance Registry System: 1-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione(114262-49-6)

Safety Data

• Hazardous Substances Data: 114262-49-6(Hazardous Substances Data)

Usage

Description

1-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione is a complex organic compound with a unique molecular structure. It is characterized by its chiral centers and functional groups, which contribute to its potential biological activities and applications.

Uses

Used in Pharmaceutical Industry:
1-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione is used as an impurity in the development of antiviral drugs, specifically for the treatment of hepatitis C. It is found in PSI-7977 (P839640), a prodrug that is metabolized to the active antiviral agent 2''-deoxy-2''-α-fluoro-β-C-methyluridine-5''-monophosphate. 1-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione has been profiled as a nucleotide inhibitor of hepatitis C virus, exerting selective inhibitory effects towards HCV NS5B polymerase and is currently being investigated in phase 3 clinical trials.

Downstream Products

• 944476-44-2 ((2R,3R,4S,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate 
• 863329-66-2 2'-deoxy-2'-fluoro-2'-methyluridine 
• 119410-95-6 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylenetetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 
• 863329-65-1 (2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate 
• 944476-44-2 C₂₄H₂₂N₂O₈ 
• 1015073-42-3 GS-461203 
• 2095551-10-1 (S)-isopropyl 2-(((S)-(((2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-di-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino) propanoate 
• 2095551-10-1 C₂₂H₃₀N₃O₁₀P 

Relevant articles and documents

IMPROVED FLUORINATION PROCESS

A process comprising (i) providing a mixture comprising a compound of formula (I) or isomers, stereoisomers, diastereomers, enantiomers or salts thereof; (ii)subjecting the mixture provided in (i) to fluorinating conditions in the presence of a fluorination agent selected from the group consisting of diethylamino (difluoro) sulfonium tetrafluoroborate and difluoro(morpholino) sulfonium tetrafluoroborate obtaining a mixture comprising a compound of formula (II) or isomers, stereoisomers diastereomers, enantiomers or salts thereof; (iii) optionally subjecting the mixture obtained in (ii) to deprotection conditions, obtaining a mixture comprising the compound of formula (III) or isomers, stereoisomers, diastereomers, enantiomers or salts thereof.