N⁶-dibenzoyl-8-N-(phenyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine

Base Information

• Chemical Name: N⁶-dibenzoyl-8-N-(phenyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine
• CAS No.: 1367204-07-6
• Molecular Formula: C₄₂H₅₄N₆O₅Si₂
• Molecular Weight: 779.099

Synonyms:N⁶-dibenzoyl-8-N-(phenyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine

Chemical Property of N⁶-dibenzoyl-8-N-(phenyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of N⁶-dibenzoyl-8-N-(phenyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine

There total 4 articles about N⁶-dibenzoyl-8-N-(phenyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-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: 93.0%

8-N-phenyl-3’,5’-O-bis(tert-butyldimethylsilyl)-2’-deoxyadenosine (1367203-94-8) + benzoyl chloride (98-88-4) → N6-dibenzoyl-8-N-(phenyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine (1367204-07-6)

Guidance literature:

With pyridine; at 25 ℃; for 16h; Inert atmosphere;

DOI:10.1021/jacs.1c07234

Reference yield:

8-bromo-2'-deoxyadenosine (14985-44-5,90968-89-1) → N6-dibenzoyl-8-N-(phenyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine (1367204-07-6)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; 1H-imidazole / 16 h / 20 °C / Inert atmosphere

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,2-dimethoxyethane / 95 °C

3: pyridine / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,2-dimethoxyethane; 2: Buchwald-Hartwig cross-coupling;

DOI:10.1002/cbic.201100573

Reference yield:

2'-deoxy-D-adenosine (958-09-8,7005-15-4) → N6-dibenzoyl-8-N-(phenyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyadenosine (1367204-07-6)

Guidance literature:

Multi-step reaction with 4 steps

1: bromine / 16 h / 20 °C / pH 5 / aq. acetate buffer

2: pyridine; 1H-imidazole / 16 h / 20 °C / Inert atmosphere

3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,2-dimethoxyethane / 95 °C

4: pyridine / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; bromine; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,2-dimethoxyethane; 3: Buchwald-Hartwig cross-coupling;

DOI:10.1002/cbic.201100573

upstream raw materials:

8-N-phenyl-3’,5’-O-bis(tert-butyldimethylsilyl)-2’-deoxyadenosine

benzoyl chloride

8-bromo-2'-deoxyadenosine

8-bromo-3′,5′-O-bis(tert-butyldimethylsilyl)-2′-deoxyadenosine

Downstream raw materials:

C₂₅H₂₄N₆O₅

C₄₆H₄₂N₆O₇

C₅₅H₅₉N₈O₈P

C₃₇H₅₂N₆O₅Si₂

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