N⁶-benzoyl-2',3'-isopropylidene-5'-(1-formyl-3-((tert-butyldiphenylsilyl)oxy)-1-propyl)-5'-deoxyadenosine

Base Information

• Chemical Name: N⁶-benzoyl-2',3'-isopropylidene-5'-(1-formyl-3-((tert-butyldiphenylsilyl)oxy)-1-propyl)-5'-deoxyadenosine
• CAS No.: 126616-48-6
• Molecular Formula: C₄₀H₄₅N₅O₆Si
• Molecular Weight: 719.913

Synonyms:N⁶-benzoyl-2',3'-isopropylidene-5'-(1-formyl-3-((tert-butyldiphenylsilyl)oxy)-1-propyl)-5'-deoxyadenosine

Chemical Property of N⁶-benzoyl-2',3'-isopropylidene-5'-(1-formyl-3-((tert-butyldiphenylsilyl)oxy)-1-propyl)-5'-deoxyadenosine

Chemical Property:

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Technology Process of N⁶-benzoyl-2',3'-isopropylidene-5'-(1-formyl-3-((tert-butyldiphenylsilyl)oxy)-1-propyl)-5'-deoxyadenosine

There total 2 articles about N⁶-benzoyl-2',3'-isopropylidene-5'-(1-formyl-3-((tert-butyldiphenylsilyl)oxy)-1-propyl)-5'-deoxyadenosine 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: 39.0%

N6-benzoyl-2',3'-isopropylidene-5'-(2-hydroxytetrahydrofuran-3-yl)-5'-deoxyadenosine (126616-46-4) + tert-butylchlorodiphenylsilane (58479-61-1) → N6-benzoyl-2',3'-isopropylidene-5'-(1-formyl-3-((tert-butyldiphenylsilyl)oxy)-1-propyl)-5'-deoxyadenosine (126616-48-6)

Guidance literature:

With 1H-imidazole; In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; at 50 ℃; for 1.33333h;

DOI:10.1021/jo00297a034

Reference yield:

N6-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanyl)-5'-deoxyadenosine (85681-04-5) → N6-benzoyl-2',3'-isopropylidene-5'-(1-formyl-3-((tert-butyldiphenylsilyl)oxy)-1-propyl)-5'-deoxyadenosine (126616-48-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / DIBAL / tetrahydrofuran; toluene / 3 h / -78 °C

2: 39 percent / imidazole / dimethylformamide; hexamethylphosphoric acid triamide / 1.33 h / 50 °C

With 1H-imidazole; diisobutylaluminium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00297a034

Reference yield: 31.0%

N-(9-{(3aR,4R,6R,6aR)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-tetrahydro-furan-3-ylmethyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-yl)-benzamide (126616-49-7) + N6-benzoyl-2',3'-isopropylidene-5'-(1-formyl-3-((tert-butyldiphenylsilyl)oxy)-1-propyl)-5'-deoxyadenosine (126616-48-6) + dimethyl diazomethylphosphonate (27491-70-9,28447-24-7,25411-73-8) → N6-benzoyl-2',3'-isopropylidene-5'-(5-((tert-butyldiphenylsilyl)oxy)-1-pentyn-3-yl)-5'-deoxyadenosine (126616-53-3)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; a) 15 min b) 5 h;

DOI:10.1021/jo00297a034

upstream raw materials:

N⁶-benzoyl-2',3'-isopropylidene-5'-(2-hydroxytetrahydrofuran-3-yl)-5'-deoxyadenosine

tert-butylchlorodiphenylsilane

N⁶-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanyl)-5'-deoxyadenosine

Downstream raw materials:

N⁶-benzoyl-2',3'-isopropylidene-5'-(5-((tert-butyldiphenylsilyl)oxy)-1-pentyn-3-yl)-5'-deoxyadenosine

2',3'-isopropylidene-5'-(5-hydroxy-1-phenyl-1-pentyn-3-yl)-5'-deoxyadenosine

2',3'-isopropylidene-5'-(5-iodo-1-phenyl-1-pentyn-3-yl)-5'-deoxyadenosine

5'-(6-amino-6-carboxy-1-phenyl-1-hexyn-3-yl)-5'-deoxyadenosine

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