5'-azido-N⁶-benzoyl-3'-(tert-butyloxycarbonylamino)-2'-O-(tert-butyldimethylsilyl)-3',5'-dideoxyadenosine

Base Information

• Chemical Name: 5'-azido-N⁶-benzoyl-3'-(tert-butyloxycarbonylamino)-2'-O-(tert-butyldimethylsilyl)-3',5'-dideoxyadenosine
• CAS No.: 420122-70-9
• Molecular Formula: C₂₈H₃₉N₉O₅Si
• Molecular Weight: 609.76

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 5'-azido-N⁶-benzoyl-3'-(tert-butyloxycarbonylamino)-2'-O-(tert-butyldimethylsilyl)-3',5'-dideoxyadenosine

There total 9 articles about 5'-azido-N⁶-benzoyl-3'-(tert-butyloxycarbonylamino)-2'-O-(tert-butyldimethylsilyl)-3',5'-dideoxyadenosine 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:

toluene-4-sulfonic acid 5-(6-benzoylamino-purin-9-yl)-3-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester → 5'-azido-N6-benzoyl-3'-(tert-butyloxycarbonylamino)-2'-O-(tert-butyldimethylsilyl)-3',5'-dideoxyadenosine (420122-70-9)

Guidance literature:

With sodium azide; ammonium chloride; In N,N-dimethyl-formamide; at 80 ℃; for 1h;

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

Reference yield:

2',5'-bis-O-(tert-butyldimethylsilyl)adenosine (65109-11-7) → 5'-azido-N6-benzoyl-3'-(tert-butyloxycarbonylamino)-2'-O-(tert-butyldimethylsilyl)-3',5'-dideoxyadenosine (420122-70-9)

Guidance literature:

Multi-step reaction with 9 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: TMSCl; pyridine / 0.5 h / 20 °C

7.2: pyridine / 2 h / 20 °C

7.3: aq. NH₃ / H₂O / 0.5 h / 20 °C

8.1: pyridine / 20 h / 20 °C

9.1: 1.62 g / NaN₃; NH₄Cl / dimethylformamide / 1 h / 80 °C

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; chloro-trimethyl-silane; sodium azide; hydroxylamine hydrochloride; hydrogen; acetic anhydride; sodium carbonate; ammonium chloride; 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) → 5'-azido-N6-benzoyl-3'-(tert-butyloxycarbonylamino)-2'-O-(tert-butyldimethylsilyl)-3',5'-dideoxyadenosine (420122-70-9)

Guidance literature:

Multi-step reaction with 8 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: TMSCl; pyridine / 0.5 h / 20 °C

6.2: pyridine / 2 h / 20 °C

6.3: aq. NH₃ / H₂O / 0.5 h / 20 °C

7.1: pyridine / 20 h / 20 °C

8.1: 1.62 g / NaN₃; NH₄Cl / dimethylformamide / 1 h / 80 °C

With pyridine; sodium tetrahydroborate; chloro-trimethyl-silane; sodium azide; hydroxylamine hydrochloride; hydrogen; sodium carbonate; ammonium chloride; 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:

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

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

2'-O-(tert-butyldimethylsilyl)-3'-(hydroxyamino)-3'-deoxyadenosine

3'-(tert-butyloxycarbonylamino)-2'-O-(tert-butyldimethylsilyl)-3'-deoxyadenosine

Downstream raw materials:

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

5'-azido-N⁶-benzoyl-2'-O-(tert-butyldimethylsilyl)-3'-(9-fluorenylmethyloxycarbonylamino)-3',5'-dideoxyadenosine

3'-amino-N⁶-benzoyl-2'-O-(tert-butyldimethylsilyl)-5'-(4-monomethoxytritylamino)-3',5'-dideoxyadenosine

N⁶-benzoyl-2'-O-(tert-butyldimethylsilyl)-3'-(9-fluorenylmethyloxycarbonylamino)-5'-(4-monomethoxytritylamino)-3',5'-dideoxyadenosine

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