N⁶-benzoyl-2′-O-(4,4′-dimethoxytrityl)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-levulinyl-adenosine-9-β-D-arabinofuranoside

Base Information

• Chemical Name: N⁶-benzoyl-2′-O-(4,4′-dimethoxytrityl)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-levulinyl-adenosine-9-β-D-arabinofuranoside
• CAS No.: 1541908-49-9
• Molecular Formula: C₅₂H₅₈N₇O₁₀P
• Molecular Weight: 972.047

Synonyms:N⁶-benzoyl-2′-O-(4,4′-dimethoxytrityl)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-levulinyl-adenosine-9-β-D-arabinofuranoside

Chemical Property of N⁶-benzoyl-2′-O-(4,4′-dimethoxytrityl)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-levulinyl-adenosine-9-β-D-arabinofuranoside

Chemical Property:

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Technology Process of N⁶-benzoyl-2′-O-(4,4′-dimethoxytrityl)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-levulinyl-adenosine-9-β-D-arabinofuranoside

There total 3 articles about N⁶-benzoyl-2′-O-(4,4′-dimethoxytrityl)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-levulinyl-adenosine-9-β-D-arabinofuranoside 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: 97.0%

N6-benzoyl-2′-O-levulinyl-5′-O-[4,4′-dimethoxytrityl]-adenosine-9-β-D-arabinofuranoside (1541908-47-7) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → N6-benzoyl-2′-O-(4,4′-dimethoxytrityl)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-levulinyl-adenosine-9-β-D-arabinofuranoside (1541908-49-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo4024182

Reference yield:

N6-benzoyl-2′-O-levulinyl-3′,5′-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-adenosine-9-β-D-arabinofuranoside (1541908-40-0) → N6-benzoyl-2′-O-(4,4′-dimethoxytrityl)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-levulinyl-adenosine-9-β-D-arabinofuranoside (1541908-49-9)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere

2: pyridine / 10 h / 20 °C / Inert atmosphere

3: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With pyridine; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1021/jo4024182

Reference yield:

N6-benzoyl-2′-O-levulinyl-adenosine-9-β-D-arabinofuranoside (1541908-42-2) → N6-benzoyl-2′-O-(4,4′-dimethoxytrityl)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-levulinyl-adenosine-9-β-D-arabinofuranoside (1541908-49-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 10 h / 20 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With pyridine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1021/jo4024182

upstream raw materials:

N⁶-benzoyl-2′-O-levulinyl-3′,5′-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-adenosine-9-β-D-arabinofuranoside

N⁶-benzoyl-2′-O-levulinyl-adenosine-9-β-D-arabinofuranoside

N⁶-benzoyl-2′-O-levulinyl-5′-O-[4,4′-dimethoxytrityl]-adenosine-9-β-D-arabinofuranoside

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

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