N⁶-benzoyl-2′-O-[acetal levulinic ester]-3′,5′-O-[1,1,3,3-tetrakis-(1-methylethyl)-1,3-disiloxanediyl]-adenosine

Base Information

• Chemical Name: N⁶-benzoyl-2′-O-[acetal levulinic ester]-3′,5′-O-[1,1,3,3-tetrakis-(1-methylethyl)-1,3-disiloxanediyl]-adenosine
• CAS No.: 1541908-21-7
• Molecular Formula: C₃₅H₅₁N₅O₉Si₂
• Molecular Weight: 741.989

Synonyms:N⁶-benzoyl-2′-O-[acetal levulinic ester]-3′,5′-O-[1,1,3,3-tetrakis-(1-methylethyl)-1,3-disiloxanediyl]-adenosine

Chemical Property of N⁶-benzoyl-2′-O-[acetal levulinic ester]-3′,5′-O-[1,1,3,3-tetrakis-(1-methylethyl)-1,3-disiloxanediyl]-adenosine

Chemical Property:

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Technology Process of N⁶-benzoyl-2′-O-[acetal levulinic ester]-3′,5′-O-[1,1,3,3-tetrakis-(1-methylethyl)-1,3-disiloxanediyl]-adenosine

There total 1 articles about N⁶-benzoyl-2′-O-[acetal levulinic ester]-3′,5′-O-[1,1,3,3-tetrakis-(1-methylethyl)-1,3-disiloxanediyl]-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: 59.0%

5-ketohexanoic acid (3128-06-1) + 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-[acetal levulinic ester]-3′,5′-O-[1,1,3,3-tetrakis-(1-methylethyl)-1,3-disiloxanediyl]-adenosine (1541908-21-7)

Guidance literature:

5-ketohexanoic acid; With cesium bicarbonate; In N,N-dimethyl-formamide; at 75 ℃; for 3h;

N-(9-((6aR,8R,9R,9aR)-2,2,4,4-tetraisopropyl-9-((methylthio)methoxy)tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-9H-purin-6-yl)benzamide; With sulfuryl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h; Inert atmosphere;

In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1021/jo4024182

Reference yield: 73.0%

N6-benzoyl-2′-O-[acetal levulinic ester]-3′,5′-O-[1,1,3,3-tetrakis-(1-methylethyl)-1,3-disiloxanediyl]-adenosine (1541908-21-7) → N6-benzoyl-2′-O-[acetal levulinic ester]-adenosine (1541908-22-8)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; at 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1021/jo4024182

Reference yield:

N6-benzoyl-2′-O-[acetal levulinic ester]-3′,5′-O-[1,1,3,3-tetrakis-(1-methylethyl)-1,3-disiloxanediyl]-adenosine (1541908-21-7) → N6-benzoyl-2′-O-[acetal levulinic ester]-5′-O-[4,4′-dimethoxytrityl]-adenosine (1541908-24-0)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine; silver nitrate; triethylamine tris(hydrogen fluoride); In tetrahydrofuran;

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

Downstream raw materials:

N⁶-benzoyl-2′-O-[acetal levulinic ester]-adenosine

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

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

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