{2-[(2R,3S,5R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(4-isobutyrylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-phosphonic acid mono-(4-methoxy-1-oxy-pyridin-2-ylmethyl) ester

Base Information

• Chemical Name: {2-[(2R,3S,5R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(4-isobutyrylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-phosphonic acid mono-(4-methoxy-1-oxy-pyridin-2-ylmethyl) ester
• CAS No.: 250649-83-3
• Molecular Formula: C₄₂H₄₇N₄O₁₁P
• Molecular Weight: 814.829
• Mol file: 250649-83-3.mol

Synonyms:

Chemical Property of {2-[(2R,3S,5R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(4-isobutyrylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-phosphonic acid mono-(4-methoxy-1-oxy-pyridin-2-ylmethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {2-[(2R,3S,5R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(4-isobutyrylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-phosphonic acid mono-(4-methoxy-1-oxy-pyridin-2-ylmethyl) ester

There total 8 articles about {2-[(2R,3S,5R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(4-isobutyrylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-phosphonic acid mono-(4-methoxy-1-oxy-pyridin-2-ylmethyl) ester 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:

4-methoxy-1-oxido-2-pyridylmethanol (64364-95-0) → {2-[(2R,3S,5R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(4-isobutyrylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-phosphonic acid mono-(4-methoxy-1-oxy-pyridin-2-ylmethyl) ester (250649-83-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / 2-chloro-5,5-dimethyl-2-oxo-2λ⁵-1,3,2-dioxaphosphinane; 4-methoxypyridine N-oxide / pyridine / 1 h

2: 72 percent / pyridine-2-aldoxime; 1,1,3,3-tetramethylguanidine / dioxane; H₂O; CHCl₃ / 1 h / pH 7

3: Bu₄NF*3H₂O / tetrahydrofuran / 2.5 h

4: 4-dimethylaminopyridine / 6 h / 70 °C

With dmap; 4-methoxypyridine N-oxide; 2-hydroxyiminomethyl-pyridine; 2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide; tetrabutyl ammonium fluoride; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; 1,4-dioxane; pyridine; chloroform; water; 1: Condensation / 2: Hydrolysis / 3: Desilylation / 4: Etherification;

DOI:10.1039/a906066i

Reference yield:

3'-O-tert-Butyldiphenylsilyl-2'-deoxycytidine → {2-[(2R,3S,5R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(4-isobutyrylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-phosphonic acid mono-(4-methoxy-1-oxy-pyridin-2-ylmethyl) ester (250649-83-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: DCC; CF₃COOH; pyridine / dimethylsulfoxide / 20 h

1.2: dimethylsulfoxide / 6 h

2.1: 75 percent / potassium azodicarboxylate; pyridine; acetic acid

3.1: 82 percent / pyridine-2-aldoximate; 1,1,3,3-tetramethylguanidine / dioxane; H₂O; CHCl₃ / 0.08 h / pH 7

4.1: 77 percent / 2-chloro-5,5-dimethyl-2-oxo-2λ⁵-1,3,2-dioxaphosphinane; 4-methoxypyridine N-oxide / pyridine / 1 h

5.1: 72 percent / pyridine-2-aldoxime; 1,1,3,3-tetramethylguanidine / dioxane; H₂O; CHCl₃ / 1 h / pH 7

6.1: Bu₄NF*3H₂O / tetrahydrofuran / 2.5 h

7.1: 4-dimethylaminopyridine / 6 h / 70 °C

With pyridine; dmap; 4-methoxypyridine N-oxide; 2-hydroxyiminomethyl-pyridine; 2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide; (E)-pyridin-2-aldoxime; tetrabutyl ammonium fluoride; potassium diazodicarboxylate; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; 1,4-dioxane; pyridine; chloroform; water; dimethyl sulfoxide; 1.1: Oxidation / 1.2: Wittig reaction / 2.1: Reduction / 3.1: Hydrolysis / 4.1: Condensation / 5.1: Hydrolysis / 6.1: Desilylation / 7.1: Etherification;

DOI:10.1039/a906066i

Reference yield:

Bis(o-chlorophenyl)[1-(3'-O-tert-butyldiphenylsilyl-2',5',6'-trideoxy-Β-D-erythro-hex-5'-enofuranosyl)-4-N-isobutyrylcytosin-6'-yl]phosphonate (250649-24-2) → {2-[(2R,3S,5R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(4-isobutyrylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl}-phosphonic acid mono-(4-methoxy-1-oxy-pyridin-2-ylmethyl) ester (250649-83-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / potassium azodicarboxylate; pyridine; acetic acid

2: 82 percent / pyridine-2-aldoximate; 1,1,3,3-tetramethylguanidine / dioxane; H₂O; CHCl₃ / 0.08 h / pH 7

3: 77 percent / 2-chloro-5,5-dimethyl-2-oxo-2λ⁵-1,3,2-dioxaphosphinane; 4-methoxypyridine N-oxide / pyridine / 1 h

4: 72 percent / pyridine-2-aldoxime; 1,1,3,3-tetramethylguanidine / dioxane; H₂O; CHCl₃ / 1 h / pH 7

5: Bu₄NF*3H₂O / tetrahydrofuran / 2.5 h

6: 4-dimethylaminopyridine / 6 h / 70 °C

With pyridine; dmap; 4-methoxypyridine N-oxide; 2-hydroxyiminomethyl-pyridine; 2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide; (E)-pyridin-2-aldoxime; tetrabutyl ammonium fluoride; potassium diazodicarboxylate; acetic acid; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; 1,4-dioxane; pyridine; chloroform; water; 1: Reduction / 2: Hydrolysis / 3: Condensation / 4: Hydrolysis / 5: Desilylation / 6: Etherification;

DOI:10.1039/a906066i

upstream raw materials:

4,4'-dimethoxytrityl chloride

4-methoxy-1-oxido-2-pyridylmethanol

Bis(o-chlorophenyl)[1-(3'-O-tert-butyldiphenylsilyl-2',5',6'-trideoxy-Β-D-erythro-hex-5'-enofuranosyl)-4-N-isobutyrylcytosin-6'-yl]phosphonate

Bis(o-chlorophenyl)[1-(3`-O-tert-butyldiphenylsilyl-2`,5`,6`-trideoxy-β-D-erythro-hexofuranosyl)-4-N-isobutyrylcytosin-6`-yl]phosphonate