5'-azido-2',3'-bis-O-tert-butyldimethylsilyl-5'-deoxy-N₆-(N-phenylcarbamoyl)adenosine

Base Information

• Chemical Name: 5'-azido-2',3'-bis-O-tert-butyldimethylsilyl-5'-deoxy-N₆-(N-phenylcarbamoyl)adenosine
• CAS No.: 1092548-24-7
• Molecular Formula: C₂₉H₄₅N₉O₄Si₂
• Molecular Weight: 639.905

Synonyms:5'-azido-2',3'-bis-O-tert-butyldimethylsilyl-5'-deoxy-N₆-(N-phenylcarbamoyl)adenosine

Chemical Property of 5'-azido-2',3'-bis-O-tert-butyldimethylsilyl-5'-deoxy-N₆-(N-phenylcarbamoyl)adenosine

Chemical Property:

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Technology Process of 5'-azido-2',3'-bis-O-tert-butyldimethylsilyl-5'-deoxy-N₆-(N-phenylcarbamoyl)adenosine

There total 4 articles about 5'-azido-2',3'-bis-O-tert-butyldimethylsilyl-5'-deoxy-N₆-(N-phenylcarbamoyl)adenosine 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%

phenyl isocyanate (103-71-9) + 5'-azido-2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxyadenosine (251296-57-8) → 5'-azido-2',3'-bis-O-tert-butyldimethylsilyl-5'-deoxy-N6-(N-phenylcarbamoyl)adenosine (1092548-24-7)

Guidance literature:

In dichloromethane; at 23 ℃; for 120h;

DOI:10.1016/j.bmcl.2009.09.083

Reference yield:

5'-deoxy-5'-chloroadenosine (892-48-8) → 5'-azido-2',3'-bis-O-tert-butyldimethylsilyl-5'-deoxy-N6-(N-phenylcarbamoyl)adenosine (1092548-24-7)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium azide / N,N-dimethyl-formamide / 1 h / 150 °C

2: N,N-dimethyl-formamide / 16 h / 20 °C

3: dichloromethane / 120 h / 20 °C

With sodium azide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.01.003

Reference yield:

adenosine (58-61-7) → 5'-azido-2',3'-bis-O-tert-butyldimethylsilyl-5'-deoxy-N6-(N-phenylcarbamoyl)adenosine (1092548-24-7)

Guidance literature:

Multi-step reaction with 4 steps

1: thionyl chloride / acetonitrile / 15 h / 20 °C

2: sodium azide / N,N-dimethyl-formamide / 1 h / 150 °C

3: N,N-dimethyl-formamide / 16 h / 20 °C

4: dichloromethane / 120 h / 20 °C

With thionyl chloride; sodium azide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmcl.2011.01.003

upstream raw materials:

phenyl isocyanate

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

5'-azido-5'-deoxyadenosine

5'-deoxy-5'-chloroadenosine

Downstream raw materials:

2',3'-bis-O-tert-butyldimethylsilyl-5'-deoxy-5'-[N-(methylcarbamoyl)amino]-N₆-(N-phenylcarbamoyl)adenosine

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