[4-¹³C]-(2S)-isopropyl 2-(((((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-trideuteromethyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Base Information

• Chemical Name: [4-¹³C]-(2S)-isopropyl 2-(((((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-trideuteromethyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
• CAS No.: 2070009-25-3
• Molecular Formula: C₂₂H₂₉FN₃O₉P
• Molecular Weight: 533.424

Synonyms:

Chemical Property of [4-¹³C]-(2S)-isopropyl 2-(((((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-trideuteromethyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Chemical Property:

Purity/Quality:

95% by HPLC; 95% atom 13C; 95% atom D ^*data from raw suppliers

PSI-7977-13CD3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: PSI-7977-13C-d3 is intended for use as an internal standard for the quantification of PSI-7977 by GC- or LC-MS. PSI-7977 is a phosphoramidate prodrug of PSI-7851, a nucleoside analog that, when phosphorylated, inhibits the RNA-dependent RNA polymerase of hepatitis C virus (EC50 = 92 nM). PSI-7977 is effective in vitro and in vivo.
• Uses: PSI-7977-13CD3 is the isotope labelled analog of PSI-7977. PSI-7977 is 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.

Technology Process of [4-¹³C]-(2S)-isopropyl 2-(((((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-trideuteromethyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

There total 8 articles about [4-¹³C]-(2S)-isopropyl 2-(((((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-trideuteromethyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 52.0%

[3-13C]-1-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-trideuteromethyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)dione (1256490-42-2) + (S)-isopropyl[(chloro(phenoxy)phosphoryl)amino]propanoate → [4-13C]-(2S)-isopropyl 2-(((((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-trideuteromethyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate (1256490-44-4,2070009-25-3)

Guidance literature:

With 1-methyl-1H-imidazole; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

DOI:10.1080/15257770.2011.614308

Reference yield:

phenyl(isopropoxy-L-alaninyl) phosphorochloridate (261909-49-3) + [3-13C]-1-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-trideuteromethyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)dione (1256490-42-2) → [4-13C]-(2S)-isopropyl 2-(((((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-trideuteromethyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate (1256490-44-4,2070009-25-3)

Guidance literature:

With 1-methyl-1H-imidazole; In tetrahydrofuran; at 20 ℃; for 1h;

Reference yield:

C23H37F3N2O8Si2 → [4-13C]-(2S)-isopropyl 2-(((((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-trideuteromethyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate (1256490-44-4,2070009-25-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / dichloromethane; hexane / 2 h / -78 - 20 °C

2.1: magnesium / tetrahydrofuran; diethyl ether / 4 h / -50 - -20 °C

2.2: 7 h / 90 °C

3.1: pyridine / 15 h / 20 °C

4.1: dimethylaminosulphur trifluoride / dichloromethane / 0.5 h / -78 - 20 °C

5.1: N-butylamine / methanol / 15 h / 20 °C

6.1: 1-methyl-1H-imidazole / tetrahydrofuran / 1 h / 0 - 20 °C

With pyridine; 1-methyl-1H-imidazole; dimethylaminosulphur trifluoride; magnesium; N-butylamine; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; 1.1: |Swern Oxidation;

DOI:10.1080/15257770.2011.614308

upstream raw materials:

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

[3-¹³C]-1-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-trideuteromethyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)dione

3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

1-((6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione

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