817204-33-4

Basic information

• Product Name: 2'-deoxy-2'-fluoro-2'-C-methylcytidine
• Synonyms: (2'R)-2'-deoxy-2'-fluoro-2'-methyl-Cytidine;4-Amino-1-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyr;2'-deoxy-2'-fluoro-2'-C-methylcytidine;PSI 6130;R 1656;ethyl 4-broMo-1-Methyl-1H-pyrrole-2-carboxylate;ethyl 4-broMo-1-Methyl-pyrrole-2-carboxylate;4-Amino-1-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimi
• CAS NO: 817204-33-4
• Molecular Formula: C₁₀H₁₄FN₃O₄
• Molecular Weight: 259.2342632
• EINECS: 200-001-2
• Product Categories: apis
• Mol File: 817204-33-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 216-218℃
• Boiling Point: 482.4±55.0 °C(Predicted)
• Appearance: /
• Density: 1.67
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 12.86±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2'-deoxy-2'-fluoro-2'-C-methylcytidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-deoxy-2'-fluoro-2'-C-methylcytidine(817204-33-4)
• EPA Substance Registry System: 2'-deoxy-2'-fluoro-2'-C-methylcytidine(817204-33-4)

Safety Data

• Hazardous Substances Data: 817204-33-4(Hazardous Substances Data)

Usage

Description

PSI-6130 is a nucleoside inhibitor of the NS5B RNA polymerase of hepatitis C virus (HCV; Ki = 4.3 μM). It inhibits HCV genotype 1b (GT-1b) Con1 and GT-1a H77 viral replication in Huh7 replicon cells using a luciferase-based assay (EC50s = 0.51 and 0.30 μM, respectively). PSI-6130 also inhibits replication of HCV GT-1b and GT-1a replicons from clinical isolates, with EC50 values ranging from 0.60 to 1.41 μM, and 0.20 to 0.43 μM, respectively, in the same assay. It has little or no activity against West Nile Virus (WNV), Dengue type 2 virus (DV), human immunodeficiency virus (HIV), or hepatitis B virus (HBV; EC90s = 46.3, >100, >100, and >10 μM, respectively).

Uses

PSI-6130 is an experimental treatment for hepatitis C. PSI-6130 is a member of a class of antiviral drugs known as nucleoside polymerase inhibitors. PSI-6130 inhibits the hepatitis C virus RNA dependant RNA polymerase called NS5B.

Upstream product

• 1583260-49-4 (3R,4R,5R)-5-(benzyloxymethyl)-3-fluoro-4-hydroxy-3-methyldihydrofuran-2(3H)-one 
• 1583260-48-3 (2R,3R,4R)-isopropyl 5-(benzyloxy)-2-fluoro-3-hydroxy-2-methyl-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate 
• 874638-98-9 N-(1-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 
• 1418141-27-1 C₂₃H₃₂FN₃O₅Si 
• 1583260-54-1 N-(1-((2R,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 
• 1583260-50-7 (3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyldihydrofuran-2(3H)-one 
• 817204-32-3 (2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate 

Downstream Products

• 1064684-24-7 (S)-2-{(4-bromophenoxy)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}-3-methylbutyric acid methyl ester 
• 1064684-28-1 (S)-2-{(4-bromophenoxy)-[(2R,3R,4R,5R)-5-(2-oxo-3-aminopyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}-3-methylbutyric acid methyl ester 
• 1064684-25-8 (S)-2-{(4-bromophenoxy)[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}propionic acid methyl ester 
• 1064684-29-2 (S)-2-{[(2R,3R,4R,5R)-5-(2-oxo-3-aminopyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phenoxyphosphorylamino}-3-methylbutyric acid methyl ester 
• 1064684-23-6 (S)-2-{[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy](phenoxy)phosphorylamino}-3-methylbutyric acid methyl ester 
• 1064684-27-0 (S)-2-{[(2R,3R,4R,5R)-5-(2-oxo-4-aminopyrimidin-1yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phenyoxy-phosphorylamino}propionic acid methyl ester 
• 1015255-46-5 (S)-2-{[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy](phenoxy)phosphorylamino}propionic acid methyl ester 
• 863329-65-1 (2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate 
• 863329-66-2 2'-deoxy-2'-fluoro-2'-methyluridine 

Relevant articles and documents

A general and enantioselective approach to pentoses: A rapid synthesis of PSI-6130, the nucleoside core of sofosbuvir

An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective α-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.

PROCESS FOR THE PREPARATION OF 2-DEOXY-2-FLUORO-2-METHYL-D-RIBOFURANOSYL NUCLEOSIDE COMPOUNDS

An improved process for the preparation of (2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine derivatives of formula I, (I), wherein R1 is selected from C1-4-alkyl is described. The (2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine derivatives of formula I have the potential to be useful as prodrugs for potent inhibitors of the Hepatitis C Virus (HCV) NS5B polymerase.

METHODS FOR TREATING HCV

This invention relates to combinations of therapeutic molecules useful for treating hepatitis C virus infection. The present invention relates to methods, uses, dosing regimens, and compositions.