N⁶-benzoyl-3'-(tert-butyloxycarbonylamino)-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine

Base Information

• Chemical Name: N⁶-benzoyl-3'-(tert-butyloxycarbonylamino)-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine
• CAS No.: 420122-77-6
• Molecular Formula: C₃₄H₅₄N₆O₆Si₂
• Molecular Weight: 699.01

Synonyms:N⁶-benzoyl-3'-(tert-butyloxycarbonylamino)-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine

Chemical Property of N⁶-benzoyl-3'-(tert-butyloxycarbonylamino)-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of N⁶-benzoyl-3'-(tert-butyloxycarbonylamino)-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine

There total 8 articles about N⁶-benzoyl-3'-(tert-butyloxycarbonylamino)-2',5'-bis-O-(tert-butyldimethylsilyl)-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%

benzoyl chloride (98-88-4) + 3'-(tert-butyloxycarbonylamino)-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine (420122-76-5) → N6-benzoyl-3'-(tert-butyloxycarbonylamino)-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine (420122-77-6)

Guidance literature:

benzoyl chloride; 3'-(tert-butyloxycarbonylamino)-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine; With pyridine; at 20 ℃; for 2h;

With ammonium hydroxide; at 20 ℃; for 0.5h;

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

Reference yield:

2',5'-bis-O-(tert-butyldimethylsilyl)adenosine (65109-11-7) → N6-benzoyl-3'-(tert-butyloxycarbonylamino)-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine (420122-77-6)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; 1H-imidazole; chromium(VI) oxide; sodium tetrahydroborate; 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-3'-(tert-butyloxycarbonylamino)-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine (420122-77-6)

Guidance literature:

Multi-step reaction with 7 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

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

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

upstream raw materials:

benzoyl chloride

3'-(tert-butyloxycarbonylamino)-2',5'-bis-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine

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

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

Downstream raw materials:

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

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

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