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

Base Information

• Chemical Name: 4-Methoxy-1-oxido-2-picolyl o-chlorophenyl[1-(3`-O-tert-butyldiphenylsilyl-2`,5`,6`-trideoxy-β-D-erythro-hexofuranosyl)-4-N-isobutyrylcytidin-6`-yl]phosphonate
• CAS No.: 250649-66-2
• Molecular Formula: C₄₃H₅₀ClN₄O₉PSi
• Molecular Weight: 861.404

Synonyms:

Chemical Property of 4-Methoxy-1-oxido-2-picolyl o-chlorophenyl[1-(3`-O-tert-butyldiphenylsilyl-2`,5`,6`-trideoxy-β-D-erythro-hexofuranosyl)-4-N-isobutyrylcytidin-6`-yl]phosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Methoxy-1-oxido-2-picolyl o-chlorophenyl[1-(3`-O-tert-butyldiphenylsilyl-2`,5`,6`-trideoxy-β-D-erythro-hexofuranosyl)-4-N-isobutyrylcytidin-6`-yl]phosphonate

There total 5 articles about 4-Methoxy-1-oxido-2-picolyl o-chlorophenyl[1-(3`-O-tert-butyldiphenylsilyl-2`,5`,6`-trideoxy-β-D-erythro-hexofuranosyl)-4-N-isobutyrylcytidin-6`-yl]phosphonate 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: 77.0%

4-methoxy-1-oxido-2-pyridylmethanol (64364-95-0) + o-Chlorophenyl[1-(3`-O-tert-butyldiphenylsilyl-2`,5`,6`-trideoxy-β-D-erythro-hexofuranosyl)-4-N-isobutyrylcytosin-6`-yl]phosphonate triethylammonium salt → 4-Methoxy-1-oxido-2-picolyl o-chlorophenyl[1-(3`-O-tert-butyldiphenylsilyl-2`,5`,6`-trideoxy-β-D-erythro-hexofuranosyl)-4-N-isobutyrylcytidin-6`-yl]phosphonate (250649-66-2)

Guidance literature:

With 4-methoxypyridine N-oxide; 2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide; In pyridine; for 1h;

DOI:10.1039/a906066i

Reference yield:

Bis(o-chlorophenyl) (triphenylphosphoranylidenemethyl)phosphonate (149741-59-3) → 4-Methoxy-1-oxido-2-picolyl o-chlorophenyl[1-(3`-O-tert-butyldiphenylsilyl-2`,5`,6`-trideoxy-β-D-erythro-hexofuranosyl)-4-N-isobutyrylcytidin-6`-yl]phosphonate (250649-66-2)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1039/a906066i

Reference yield:

3'-O-tert-Butyldiphenylsilyl-2'-deoxycytidine → 4-Methoxy-1-oxido-2-picolyl o-chlorophenyl[1-(3`-O-tert-butyldiphenylsilyl-2`,5`,6`-trideoxy-β-D-erythro-hexofuranosyl)-4-N-isobutyrylcytidin-6`-yl]phosphonate (250649-66-2)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1039/a906066i

upstream raw materials:

4-methoxy-1-oxido-2-pyridylmethanol

Bis(o-chlorophenyl) (triphenylphosphoranylidenemethyl)phosphonate

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

Downstream raw materials:

{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

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