N⁶-benzoyl-5'-O-[bis(allyloxy)phosphoryl]-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine

Base Information

• Chemical Name: N⁶-benzoyl-5'-O-[bis(allyloxy)phosphoryl]-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine
• CAS No.: 478050-94-1
• Molecular Formula: C₄₅H₄₇N₅O₁₂P₂
• Molecular Weight: 911.842

Synonyms:N⁶-benzoyl-5'-O-[bis(allyloxy)phosphoryl]-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine

Chemical Property of N⁶-benzoyl-5'-O-[bis(allyloxy)phosphoryl]-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine

Chemical Property:

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Technology Process of N⁶-benzoyl-5'-O-[bis(allyloxy)phosphoryl]-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine

There total 6 articles about N⁶-benzoyl-5'-O-[bis(allyloxy)phosphoryl]-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)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: 84.0%

Phosphoric acid (2R,3R,4R,5R)-5-(6-benzoylamino-purin-9-yl)-2-(bis-allyloxy-phosphanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-3-yl ester dibenzyl ester → N6-benzoyl-5'-O-[bis(allyloxy)phosphoryl]-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine (478050-94-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 5 ℃; for 1h;

DOI:10.1021/jo0260443

Reference yield:

Dibenzyl N,N-diisopropylphosphoramidite (108549-23-1) → N6-benzoyl-5'-O-[bis(allyloxy)phosphoryl]-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine (478050-94-1)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrazole / CH₂Cl₂ / 1 h

2: 3.5 percent / mCPBA / CH₂Cl₂ / 1 h

3: 74 percent / acetic acid / H₂O / 2 h / 20 °C

4: tetrazole / CH₂Cl₂ / 2 h

5: 84 percent / mCPBA / CH₂Cl₂ / 1 h / 0 - 5 °C

With 1H-tetrazole; acetic acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water;

DOI:10.1021/jo0260443

Reference yield:

5'-O-dimethoxytrityl-2'-O-(4-methoxybenzyl)-N6-benzoyl adenosine (80015-60-7) → N6-benzoyl-5'-O-[bis(allyloxy)phosphoryl]-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine (478050-94-1)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrazole / CH₂Cl₂ / 1 h

2: 3.5 percent / mCPBA / CH₂Cl₂ / 1 h

3: 74 percent / acetic acid / H₂O / 2 h / 20 °C

4: tetrazole / CH₂Cl₂ / 2 h

5: 84 percent / mCPBA / CH₂Cl₂ / 1 h / 0 - 5 °C

With 1H-tetrazole; acetic acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water;

DOI:10.1021/jo0260443

upstream raw materials:

Dibenzyl N,N-diisopropylphosphoramidite

5'-O-dimethoxytrityl-2'-O-(4-methoxybenzyl)-N⁶-benzoyl adenosine

N⁶-benzoyl-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine

N⁶-benzoyl-5'-O-dimethoxytrityl-2'-O-(4-methoxybenzyl)-3'-[[bis(benzyloxy)phosphoryl]oxy]adenosine

Downstream raw materials:

5'-O-[bis(allyloxy)phosphoryl]-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine

3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)-5'-O-phosphate adenosine

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