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

Base Information

• Chemical Name: 5'-O-[bis(allyloxy)phosphoryl]-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine
• CAS No.: 478050-95-2
• Molecular Formula: C₃₈H₄₃N₅O₁₁P₂
• Molecular Weight: 807.734

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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

There total 7 articles about 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: 68.0%

N6-benzoyl-5'-O-[bis(allyloxy)phosphoryl]-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine (478050-94-1) → 5'-O-[bis(allyloxy)phosphoryl]-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine (478050-95-2)

Guidance literature:

With propylamine; In tetrahydrofuran; for 3h;

DOI:10.1021/jo0260443

Reference yield:

Dibenzyl N,N-diisopropylphosphoramidite (108549-23-1) → 5'-O-[bis(allyloxy)phosphoryl]-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine (478050-95-2)

Guidance literature:

Multi-step reaction with 6 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

6: 68 percent / n-propylamine / tetrahydrofuran / 3 h

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

DOI:10.1021/jo0260443

Reference yield:

5'-O-dimethoxytrityl-2'-O-(4-methoxybenzyl)-N6-benzoyl adenosine (80015-60-7) → 5'-O-[bis(allyloxy)phosphoryl]-3'-O-[bis(benzyloxy)phosphoryl]-2'-O-(4-methoxybenzyl)adenosine (478050-95-2)

Guidance literature:

Multi-step reaction with 6 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

6: 68 percent / n-propylamine / tetrahydrofuran / 3 h

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

DOI:10.1021/jo0260443

upstream raw materials:

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

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

Downstream raw materials:

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

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