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

Base Information

Chemical Name:N-(9-((2R,3R,4R,5R)-4-amino-5-(azidomethyl)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide
CAS No.:420122-71-0
Molecular Formula:C₂₃H₃₁N₉O₃Si
Molecular Weight:509.643
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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

There total 22 articles about N-(9-((2R,3R,4R,5R)-4-amino-5-(azidomethyl)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide 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: 85.0%

: 420122-70-9
5'-azido-N⁶-benzoyl-3'-(tert-butyloxycarbonylamino)-2'-O-(tert-butyldimethylsilyl)-3',5'-dideoxyadenosine

: 420122-71-0
N-(9-((2R,3R,4R,5R)-4-amino-5-(azidomethyl)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 40h;
DOI:10.1016/S0040-4020(01)01185-1

Reference yield:

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

: 420122-71-0
N-(9-((2R,3R,4R,5R)-4-amino-5-(azidomethyl)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide

Guidance literature:: With Amberlyst-15; In methanol; dichloromethane; at 20 ℃; for 2h;

Reference yield:

: 65109-11-7
2',5'-bis-O-(tert-butyldimethylsilyl)adenosine

: 420122-71-0
N-(9-((2R,3R,4R,5R)-4-amino-5-(azidomethyl)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide

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: 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

10.1: 85 percent / TFA / CH₂Cl₂ / 40 h / 20 °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