5',3'-bis(O-tert-butyldimethylsilyl)-6-N-(6-nitroveratryloxycarbonyl)-2'-deoxyadenosine

Base Information

• Chemical Name: 5',3'-bis(O-tert-butyldimethylsilyl)-6-N-(6-nitroveratryloxycarbonyl)-2'-deoxyadenosine
• CAS No.: 243657-06-9
• Molecular Formula: C₃₂H₅₀N₆O₉Si₂
• Molecular Weight: 718.955
• Mol file: 243657-06-9.mol

Synonyms:5',3'-bis(O-tert-butyldimethylsilyl)-6-N-(6-nitroveratryloxycarbonyl)-2'-deoxyadenosine

Chemical Property of 5',3'-bis(O-tert-butyldimethylsilyl)-6-N-(6-nitroveratryloxycarbonyl)-2'-deoxyadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5',3'-bis(O-tert-butyldimethylsilyl)-6-N-(6-nitroveratryloxycarbonyl)-2'-deoxyadenosine

There total 2 articles about 5',3'-bis(O-tert-butyldimethylsilyl)-6-N-(6-nitroveratryloxycarbonyl)-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: 63.0%

3',5'-bis-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine (51549-32-7) + 6-nitroveratryloxycarbonyltetrazolide → 5',3'-bis(O-tert-butyldimethylsilyl)-6-N-(6-nitroveratryloxycarbonyl)-2'-deoxyadenosine (243657-06-9)

Guidance literature:

In tetrahydrofuran; at 20 - 70 ℃;

DOI:10.1021/jo990479h

Reference yield:

nitroveratryloxycarbonyl chloride (42855-00-5) → 5',3'-bis(O-tert-butyldimethylsilyl)-6-N-(6-nitroveratryloxycarbonyl)-2'-deoxyadenosine (243657-06-9)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 0 - 20 °C

2: 63 percent / tetrahydrofuran / 20 - 70 °C

With triethylamine; In tetrahydrofuran; 1: Acylation / 2: Acylation;

DOI:10.1021/jo990479h

Reference yield:

5',3'-bis(O-tert-butyldimethylsilyl)-6-N-(6-nitroveratryloxycarbonyl)-2'-deoxyadenosine (243657-06-9) → 6-N-(6-nitroveratryloxycarbonyl)-2'-deoxyadenosine (243657-07-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1.5h;

DOI:10.1021/jo990479h

upstream raw materials:

3',5'-bis-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine

nitroveratryloxycarbonyl chloride

Downstream raw materials:

6-N-(6-nitroveratryloxycarbonyl)-2'-deoxyadenosine

5'-O-(4,4'-dimethoxytrityl)-6-N-(6-nitroveratryloxycarbonyl)-2'-deoxyadenosine

5'-O-(4,4'-dimethoxytrityl)-6-N-(6-nitroveratryloxycarbonyl)-2'-deoxyadenosine 3'-O-(S-pivaloyl-2-thioethyl) N,N-diisopropylphosphoramidite