N⁶-benzoyl-2′-O-(acetyl levulinic ester)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-(4,4′-dimethoxytrityl)-adenosine

Base Information

• Chemical Name: N⁶-benzoyl-2′-O-(acetyl levulinic ester)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-(4,4′-dimethoxytrityl)-adenosine
• CAS No.: 1541908-27-3
• Molecular Formula: C₅₃H₆₀N₇O₁₁P
• Molecular Weight: 1002.07
• Mol file: 1541908-27-3.mol

Synonyms:N⁶-benzoyl-2′-O-(acetyl levulinic ester)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-(4,4′-dimethoxytrityl)-adenosine

Chemical Property of N⁶-benzoyl-2′-O-(acetyl levulinic ester)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-(4,4′-dimethoxytrityl)-adenosine

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁶-benzoyl-2′-O-(acetyl levulinic ester)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-(4,4′-dimethoxytrityl)-adenosine

There total 5 articles about N⁶-benzoyl-2′-O-(acetyl levulinic ester)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-(4,4′-dimethoxytrityl)-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: 71.0%

N6-benzoyl-2′-O-[acetal levulinic ester]-5′-O-[4,4′-dimethoxytrityl]-adenosine (1541908-24-0) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → N6-benzoyl-2′-O-(acetyl levulinic ester)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-(4,4′-dimethoxytrityl)-adenosine (1541908-27-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jo4024182

Reference yield:

5-ketohexanoic acid (3128-06-1) → N6-benzoyl-2′-O-(acetyl levulinic ester)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-(4,4′-dimethoxytrityl)-adenosine (1541908-27-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: cesium bicarbonate / N,N-dimethyl-formamide / 3 h / 75 °C

1.2: 3 h / 0 - 20 °C / Inert atmosphere

1.3: 15 h / 20 °C / Inert atmosphere

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

3.1: silver nitrate; pyridine / tetrahydrofuran / 1.2 h / 20 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

With pyridine; cesium bicarbonate; silver nitrate; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo4024182

Reference yield:

N-benzoyl-3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1, 3-diyl)-2′-O-[(methylthio)methyl]adenosine (139434-69-8) → N6-benzoyl-2′-O-(acetyl levulinic ester)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-(4,4′-dimethoxytrityl)-adenosine (1541908-27-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: cesium bicarbonate / N,N-dimethyl-formamide / 3 h / 75 °C

1.2: 3 h / 0 - 20 °C / Inert atmosphere

1.3: 15 h / 20 °C / Inert atmosphere

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

3.1: silver nitrate; pyridine / tetrahydrofuran / 1.2 h / 20 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

With pyridine; cesium bicarbonate; silver nitrate; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo4024182

upstream raw materials:

5-ketohexanoic acid

N-benzoyl-3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1, 3-diyl)-2′-O-[(methylthio)methyl]adenosine

N⁶-benzoyl-2′-O-[acetal levulinic ester]-5′-O-[4,4′-dimethoxytrityl]-adenosine

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