SofosBuvir impurity 21

Base Information

• Chemical Name: SofosBuvir impurity 21
• CAS No.: 1496552-50-1
• Molecular Formula: C₂₂H₂₉ClN₃O₉P
• Molecular Weight: 545.914
• Mol file: 1496552-50-1.mol

Synonyms:

Chemical Property of SofosBuvir impurity 21

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Chloro(R)-PhosphorylSofosbuvir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Chloro (R)-Phosphoryl Sofosbuvir can be used to synthesize nucleoside phosphoramidate compounds and 2''-chloro nucleotide analogs?that are potential treatment of?hepatitis C virus (HCV)?infection. Chloro (R)-Phosphoryl Sofosbuvir is also a phosphorus epimer of Chloro Sofosbuvir (C382095) and a related compound of Sofosbuvir (P839640).

Technology Process of SofosBuvir impurity 21

There total 50 articles about SofosBuvir impurity 21 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: 85.0%

1-((2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (1496551-72-4) + (R)-2-((R)-(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphorylamino)propionic acid isopropyl ester (1627824-09-2) → MK-3682 (1496551-77-9,1496552-50-1)

Guidance literature:

With 2,6-dimethylpyridine; aluminum (III) chloride; In tetrahydrofuran; at 5 - 50 ℃; Reagent/catalyst; Solvent; Inert atmosphere;

Reference yield: 57.0%

1-((2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (1496551-72-4) + (R)-2-((R)-(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphorylamino)propionic acid isopropyl ester (1627824-09-2) → ((S)-(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-chloro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-D-alanine isopropyl ester (1496551-77-9,1496552-50-1)

Guidance literature:

1-((2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione; With tert-butylmagnesium chloride; In tetrahydrofuran; at 0 ℃; for 0.5h;

(R)-2-((R)-(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphorylamino)propionic acid isopropyl ester; In tetrahydrofuran; at 0 ℃; for 24h;

Reference yield: 55.0%

1-((2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (1496551-72-4) + isopropyl (2R)-2-[[(2,3,4,5,6-pentafluorophenoxy)-phenoxy-phosphoryl]amino]propanoate (1627824-09-2) → MK-3682 (1496551-77-9,1496552-50-1)

Guidance literature:

1-((2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione; With tert-butylmagnesium chloride; In tetrahydrofuran; at 0 ℃; for 0.5h;

isopropyl (2R)-2-[[(2,3,4,5,6-pentafluorophenoxy)-phenoxy-phosphoryl]amino]propanoate; In tetrahydrofuran; at 0 ℃; for 24h;

upstream raw materials:

(S)-2-[(4-nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester

1-((2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

2'-deoxy-2'-chloro-2'-C-methyl-3',5'-di-O-benzoyl-N⁴-benzoylcytidine

C₂₄H₂₁ClN₂O₇

Refernces

• 1、 Chris Krueger,Chen, Hui-Ju,Randolph, John T.,Brown, Brian S.,Halvorsen, Geoff T.,Heyman, Howard R.,Li, Tongmei,Marvin, Christopher C.,Shanley, Jason P.,Voight, Eric A.,Bow, Daniel A.J.,Van Handel, Cecilia,Peterkin, Vincent,Carr, Robert A.,Stolarik, DeAnne,Dekhtyar, Tatyana,Irvin, Michelle L.,Krishnan, Preethi,Henry, Rodger F.,Wagner, Rolf,DeGoey, David A.. "Synthesis and evaluation of 2′-dihalo ribonucleotide prodrugs with activity against hepatitis C virus". . . Retrieved 2019/11/26.
• 2、 Orr, Robert K.,Dunn, Jamie M. McCabe,Nolting, Andrew,Hyde, Alan M.,Ashley, Eric R.,Leone, Joseph,Sirota, Eric,Jurica, Jon A.,Gibson, Andrew,Wise, Christopher,Oliver, Steven,Ruck, Rebecca T.. "New reactions and processes for the efficient synthesis of a HCV NS5b prodrug". . p. 2519 - 2525. Retrieved 2018/06/11.