N⁶-benzoyl-3′-O-(tert-butyldimethylsilyl)-2′-(N-tert-butyloxycarbonyl-L-alanine)amido-3′-deoxyadenosine

Base Information

• Chemical Name: N⁶-benzoyl-3′-O-(tert-butyldimethylsilyl)-2′-(N-tert-butyloxycarbonyl-L-alanine)amido-3′-deoxyadenosine
• CAS No.: 1452385-21-5
• Molecular Formula: C₃₁H₄₅N₇O₇Si
• Molecular Weight: 655.827

Synonyms:N⁶-benzoyl-3′-O-(tert-butyldimethylsilyl)-2′-(N-tert-butyloxycarbonyl-L-alanine)amido-3′-deoxyadenosine

Chemical Property of N⁶-benzoyl-3′-O-(tert-butyldimethylsilyl)-2′-(N-tert-butyloxycarbonyl-L-alanine)amido-3′-deoxyadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of N⁶-benzoyl-3′-O-(tert-butyldimethylsilyl)-2′-(N-tert-butyloxycarbonyl-L-alanine)amido-3′-deoxyadenosine

There total 2 articles about N⁶-benzoyl-3′-O-(tert-butyldimethylsilyl)-2′-(N-tert-butyloxycarbonyl-L-alanine)amido-3′-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: 78.0%

N6-benzoyl-3′,5′-bis-O-(tert-butyl-dimethylsilyl)-2′-(S)-methylcarbamate2′-deoxyadenosine (1452385-19-1) → N6-benzoyl-3′-O-(tert-butyldimethylsilyl)-2′-(N-tert-butyloxycarbonyl-L-alanine)amido-3′-deoxyadenosine (1452385-21-5)

Guidance literature:

In tetrahydrofuran; water; trifluoroacetic acid; at 0 ℃; for 12h;

DOI:10.1039/c3ob41206g

Reference yield:

6-N-benzoyl-2′-azido-3′,5′-bis-O-(tert-butyldimethylsilyl)-2′-deoxyadenosine (1245200-31-0) → N6-benzoyl-3′-O-(tert-butyldimethylsilyl)-2′-(N-tert-butyloxycarbonyl-L-alanine)amido-3′-deoxyadenosine (1452385-21-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogen / methanol / 12 h / 20 °C / 760.05 Torr

2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.25 h / 0 °C

2.2: 18 h / 20 °C

3.1: tetrahydrofuran; trifluoroacetic acid; water / 12 h / 0 °C

With dmap; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; dichloromethane; water; trifluoroacetic acid;

DOI:10.1039/c3ob41206g

Reference yield:

N6-benzoyl-3′-O-(tert-butyldimethylsilyl)-2′-(N-tert-butyloxycarbonyl-L-alanine)amido-3′-deoxyadenosine (1452385-21-5) + 5'-O-(4,4'-dimethoxytrityl)-N-acetyl-2'-deoxycytidine 3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite (157543-67-4,157543-68-5,154110-40-4) → C66H80N11O16PSi

Guidance literature:

N⁶-benzoyl-3′-O-(tert-butyldimethylsilyl)-2′-(N-tert-butyloxycarbonyl-L-alanine)amido-3′-deoxyadenosine; 5'-O-(4,4'-dimethoxytrityl)-N-acetyl-2'-deoxycytidine 3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite; With 1H-tetrazole; In dichloromethane; acetonitrile; at 20 ℃; for 1h; Inert atmosphere;

With pyridine; iodine; In tetrahydrofuran; dichloromethane; water; acetonitrile; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1039/c3ob41206g

upstream raw materials:

6-N-benzoyl-2′-azido-3′,5′-bis-O-(tert-butyldimethylsilyl)-2′-deoxyadenosine

N⁶-benzoyl-3′,5′-bis-O-(tert-butyl-dimethylsilyl)-2′-(S)-methylcarbamate2′-deoxyadenosine

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