N⁶-benzoyl-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-[(N-(9-fluorenylmethyloxycarbonyl)thiocarbamoyl)amino]-3'-deoxyadenosine

Base Information

• Chemical Name: N⁶-benzoyl-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-[(N-(9-fluorenylmethyloxycarbonyl)thiocarbamoyl)amino]-3'-deoxyadenosine
• CAS No.: 420122-79-8
• Molecular Formula: C₄₅H₅₇N₇O₆SSi₂
• Molecular Weight: 880.228

Synonyms:N⁶-benzoyl-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-[(N-(9-fluorenylmethyloxycarbonyl)thiocarbamoyl)amino]-3'-deoxyadenosine

Chemical Property of N⁶-benzoyl-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-[(N-(9-fluorenylmethyloxycarbonyl)thiocarbamoyl)amino]-3'-deoxyadenosine

Chemical Property:

Purity/Quality:

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Technology Process of N⁶-benzoyl-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-[(N-(9-fluorenylmethyloxycarbonyl)thiocarbamoyl)amino]-3'-deoxyadenosine

There total 10 articles about N⁶-benzoyl-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-[(N-(9-fluorenylmethyloxycarbonyl)thiocarbamoyl)amino]-3'-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: 95.0%

9-fluorenylmethoxycarbonyl isothiocyanate (199915-38-3) + N-(9-((2R,3R,4R,5S)-4-amino-3-((tert-butyldimethylsilyl)oxy)-5-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide (420122-78-7) → N6-benzoyl-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-[(N-(9-fluorenylmethyloxycarbonyl)thiocarbamoyl)amino]-3'-deoxyadenosine (420122-79-8)

Guidance literature:

In dichloromethane; at 20 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(01)01185-1

Reference yield:

2',5'-bis-O-(tert-butyldimethylsilyl)adenosine (65109-11-7) → N6-benzoyl-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-[(N-(9-fluorenylmethyloxycarbonyl)thiocarbamoyl)amino]-3'-deoxyadenosine (420122-79-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: pyridine; CrO₃; Ac₂O / molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 20 °C

2.1: 5.16 g / pyridine; hydroxylamine hydrochloride / 14 h / 20 °C

3.1: 3.34 g / aq. TFA / 0.33 h / 0 °C

4.1: 82 percent / NaBH₄; AcOH / 2 h / 5 °C

5.1: H₂ / Pd/C / acetic acid; H₂O / 20 h / 20 °C

6.1: 2.22 g / Na₂CO₃ / tetrahydrofuran; H₂O / 2 h / 20 °C

7.1: 86 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

8.1: pyridine / 2 h / 20 °C

8.2: 95 percent / aq. NH₃ / 0.5 h / 20 °C

9.1: 82 percent / AlCl₃ / CH₂Cl₂ / 0.75 h / 0 °C

10.1: 95 percent / CH₂Cl₂ / 0.17 h / 20 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; sodium tetrahydroborate; aluminium trichloride; hydroxylamine hydrochloride; hydrogen; acetic anhydride; sodium carbonate; acetic acid; trifluoroacetic acid; palladium on activated charcoal; 4 A molecular sieve; In tetrahydrofuran; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)01185-1

Reference yield:

9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine (86734-95-4) → N6-benzoyl-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-[(N-(9-fluorenylmethyloxycarbonyl)thiocarbamoyl)amino]-3'-deoxyadenosine (420122-79-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 5.16 g / pyridine; hydroxylamine hydrochloride / 14 h / 20 °C

2.1: 3.34 g / aq. TFA / 0.33 h / 0 °C

3.1: 82 percent / NaBH₄; AcOH / 2 h / 5 °C

4.1: H₂ / Pd/C / acetic acid; H₂O / 20 h / 20 °C

5.1: 2.22 g / Na₂CO₃ / tetrahydrofuran; H₂O / 2 h / 20 °C

6.1: 86 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

7.1: pyridine / 2 h / 20 °C

7.2: 95 percent / aq. NH₃ / 0.5 h / 20 °C

8.1: 82 percent / AlCl₃ / CH₂Cl₂ / 0.75 h / 0 °C

9.1: 95 percent / CH₂Cl₂ / 0.17 h / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; aluminium trichloride; hydroxylamine hydrochloride; hydrogen; sodium carbonate; acetic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)01185-1

upstream raw materials:

9-fluorenylmethoxycarbonyl isothiocyanate

N-(9-((2R,3R,4R,5S)-4-amino-3-((tert-butyldimethylsilyl)oxy)-5-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide

2',5'-bis-O-(tert-butyldimethylsilyl)adenosine

9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine

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