1190308-01-0

Basic information

• Product Name: PSI-7976
• Synonyms: PSI-7976;N-[[P(R),2'R]-2'-Deoxy-2'-fluoro-2'-methyl-P-phenyl-5'-uridylyl]-L-alanine 1-methylethyl ester;Sofosbuvir Impurity 19;Sofosbuvir (R)-Phosphate;(S)-isopropyl 2-((R)-(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorylamino)propanoate;isopropyl ((R)-(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-Lalaninate
• CAS NO: 1190308-01-0
• Molecular Formula: C₂₂H₂₉FN₃O₉P
• Molecular Weight: 529.4525242
• Mol File: 1190308-01-0.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Density: 1.41±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Aceatae (Slightly)
• PKA: 9.39±0.10(Predicted)
• CAS DataBase Reference: PSI-7976(CAS DataBase Reference)
• NIST Chemistry Reference: PSI-7976(1190308-01-0)
• EPA Substance Registry System: PSI-7976(1190308-01-0)

Safety Data

• Hazardous Substances Data: 1190308-01-0(Hazardous Substances Data)

Usage

Uses

Sofosbuvir (R)-Phosphate is an impurity of PSI-7977 (P839640), a prodrug that is metabolized to the active antiviral agent 2''-deoxy-2''-α-fluoro-β-C-methyluridine-5''-monophosphate and is currently being investigated in phase 3 clinical trials for the treatment of hepatitis C. Studies have profiled PSI-7977 as a nucleotide inhibitor of hepatitis C virus, exerting selective inhibitory effects towards HCV NS5B polymerase.

Upstream product

• 863329-66-2 2'-deoxy-2'-fluoro-2'-methyluridine 
• 770-12-7 O-phenyl phosphorodichloridate 
• 39613-92-8 alanine isopropyl ester hydrochloride 
• 1334513-02-8 (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester 
• 1337529-56-2 (S)-2-[(S)-(2,3,4,5,6-pentafluoro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester 
• 261909-49-3 phenyl(isopropoxy-L-alaninyl) phosphorochloridate 
• 108-95-2 phenol 
• 793-10-2 p-nitrophenyl phenyl phosphorochloridate 
• 1256490-48-8 (S)-2-[(4-nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester 
• 1256490-49-9 (S)-2-[(R)-(4-nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester 
• 1256490-31-9 (S)-2-[(S)-(4-nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester 

Relevant articles and documents

Method for preparing sofosbuvir

The invention discloses a method for preparing sofosbuvir. The method comprises the following steps: reacting tetrahydrofuran with a tetrahydrofuran solution of a material A, a material B, DMAP and ananiline compound under the protection of nitrogen, and monitoring the reaction by TLC until the reaction of the material A is finished, wherein the aniline compound is N,N-dimethylaniline or N,N-diethylaniline; and carrying out post-treatment on the obtained reaction product. The method for preparing sofosbuvir has the advantages of high reaction efficiency, high product yield (up to 90% or above), high purity (up to 98% or above), easiness in industrial large-scale production and great application values.

Novel process for preparing sofosbuvir

The invention provides a preparation process for sofosbuvir. According to the invention, in a butting process of two key fragments, tert-butylmagnesium chloride/lithium chloride is used as base, so selectivity of the base is improved; the conversion rate

Mechanism-Based Solution to the ProTide Synthesis Problem: Selective Access to Sofosbuvir, Acelarin, and INX-08189

A general and efficient method for the synthesis of pronucleotide (ProTide) 5'-phosphoramidate monoesters is reported. This method consists of a highly stereoselective 5'-phosphorylation mediated by dimethylaluminum chloride to afford the desired target ProTides in excellent yields without employing 3'-protection strategies. The application of this methodology to the synthesis of a number of pharmaceutically relevant compounds currently marketed or under investigation in clinical research is demonstrated.