1334513-10-8

Basic information

• Product Name: L-Alanine, N-[[P(S),2'R]-2'-deoxy-2'-fluoro-2'-Methyl-P-phenyl-5'-cytidylyl]-, 1-Methylethyl ester
• Synonyms: L-Alanine, N-[[P(S),2'R]-2'-deoxy-2'-fluoro-2'-Methyl-P-phenyl-5'-cytidylyl]-, 1-Methylethyl ester;N-[[P(S),2'R]-2'-Deoxy-2'-fluoro-2'-methyl-P-phenyl-5'-cytidylyl]-L-alanine 1-methylethyl ester;Sofosbuvir impurity J
• CAS NO: 1334513-10-8
• Molecular Formula: C₂₂H₃₀FN₄O₈P
• Molecular Weight: 528.4677642
• Mol File: 1334513-10-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: L-Alanine, N-[[P(S),2'R]-2'-deoxy-2'-fluoro-2'-Methyl-P-phenyl-5'-cytidylyl]-, 1-Methylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Alanine, N-[[P(S),2'R]-2'-deoxy-2'-fluoro-2'-Methyl-P-phenyl-5'-cytidylyl]-, 1-Methylethyl ester(1334513-10-8)
• EPA Substance Registry System: L-Alanine, N-[[P(S),2'R]-2'-deoxy-2'-fluoro-2'-Methyl-P-phenyl-5'-cytidylyl]-, 1-Methylethyl ester(1334513-10-8)

Safety Data

• Hazardous Substances Data: 1334513-10-8(Hazardous Substances Data)

Upstream product

• 817204-33-4 (2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine 
• 1334513-02-8 (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester 
• 770-12-7 O-phenyl phosphorodichloridate 
• 39613-92-8 alanine isopropyl ester hydrochloride 

Relevant articles and documents

4'-FLUORO-2'-METHYL SUBSTITUTED NUCLEOSIDE DERIVATIVES AS INHIBITORS OF HCV RNA REPLICATION

Cytidine nucleoside analogues of Formula I, wherein the variables are as described herein, in combination with uridine nucleoside analogues of Formula II, wherein the variables are as described herein, produce a synergistic effect on the inhibition of HCV

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.

Synthesis of diastereomerically pure nucleotide phosphoramidates

Prodrugs of therapeutic nucleoside monophosphates masked as phosphoramidate derivatives have become an increasingly important class of antiviral drugs in pharmaceutical research for delivering nucleotides in vitro and in vivo. Conventionally, phosphoramidate derivatives are prepared as a mixture of two diastereomers. We report a class of stable phosphoramidating reagents containing an amino acid ester and two phenolic groups, one unsubstituted and the other with electron-withdrawing substituents. The reagents can be isolated as single diastereomers and reacted with the 5′-hydroxyl group of nucleosides through selective nucleophilic displacement of the substituted phenol to prepare single diastereomer phosphoramidate products. This method has been used to prepare the HCV clinical candidate PSI-7977 in high yield and high diastereomeric purity.