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

Base Information

• Chemical Name: Bis(o-chlorophenyl)[1-(3'-O-tert-butyldiphenylsilyl-2',5',6'-trideoxy-Β-D-erythro-hex-5'-enofuranosyl)-4-N-isobutyrylcytosin-6'-yl]phosphonate
• CAS No.: 250649-24-2
• Molecular Formula: C₄₂H₄₄Cl₂N₃O₇PSi
• Molecular Weight: 832.793
• Mol file: 250649-24-2.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about Bis(o-chlorophenyl)[1-(3'-O-tert-butyldiphenylsilyl-2',5',6'-trideoxy-Β-D-erythro-hex-5'-enofuranosyl)-4-N-isobutyrylcytosin-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:

Bis(o-chlorophenyl) (triphenylphosphoranylidenemethyl)phosphonate (149741-59-3) + 3'-O-tert-Butyldiphenylsilyl-2'-deoxycytidine → 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)

Guidance literature:

3'-O-tert-Butyldiphenylsilyl-2'-deoxycytidine; With pyridine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dimethyl sulfoxide; for 20h;

Bis(o-chlorophenyl) (triphenylphosphoranylidenemethyl)phosphonate; In dimethyl sulfoxide; for 6h;

DOI:10.1039/a906066i

Reference yield: 75.0%

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) → Bis(o-chlorophenyl)[1-(3`-O-tert-butyldiphenylsilyl-2`,5`,6`-trideoxy-β-D-erythro-hexofuranosyl)-4-N-isobutyrylcytosin-6`-yl]phosphonate (250649-33-3)

Guidance literature:

With pyridine; potassium diazodicarboxylate; acetic acid;

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:

Bis(o-chlorophenyl) (triphenylphosphoranylidenemethyl)phosphonate

Downstream raw materials:

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

{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

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