N⁶-benzoyl-2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-(S)-methylcarbamate-3′-deoxyadenosine

Base Information

• Chemical Name: N⁶-benzoyl-2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-(S)-methylcarbamate-3′-deoxyadenosine
• CAS No.: 1452385-18-0
• Molecular Formula: C₃₇H₅₉N₇O₇Si₂
• Molecular Weight: 770.089

Synonyms:N⁶-benzoyl-2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-(S)-methylcarbamate-3′-deoxyadenosine

Chemical Property of N⁶-benzoyl-2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-(S)-methylcarbamate-3′-deoxyadenosine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of N⁶-benzoyl-2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-(S)-methylcarbamate-3′-deoxyadenosine

There total 2 articles about N⁶-benzoyl-2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-(S)-methylcarbamate-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:

L-N-Boc-Ala (15761-38-3) + N-(9-((2R,3R,4R,5S)-4-amino-3-((tert-butyldimethylsilyl)oxy)-5-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide (420122-78-7) → N6-benzoyl-2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-(S)-methylcarbamate-3′-deoxyadenosine (1452385-18-0)

Guidance literature:

L-N-Boc-Ala; With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 0.25h;

3′-amino-N⁶-benzoyl-2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-deoxyadenosine; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1039/c3ob41206g

Reference yield:

6-N-benzoyl-3′-azido-2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-deoxyadenosine (1142928-70-8) → N6-benzoyl-2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-(S)-methylcarbamate-3′-deoxyadenosine (1452385-18-0)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1039/c3ob41206g

Reference yield: 64.0%

N6-benzoyl-2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-(S)-methylcarbamate-3′-deoxyadenosine (1452385-18-0) → N6-benzoyl-2′-O-(tert-butyldimethylsilyl)-3′-(N-tert-butyloxycarbonyl-L-alanine)amido-3′-deoxyadenosine (1452385-20-4)

Guidance literature:

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

DOI:10.1039/c3ob41206g

upstream raw materials:

L-N-Boc-Ala

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

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

Downstream raw materials:

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

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