2',3'-di-O-acetyl-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl(S_R)>adenosine

Base Information

• Chemical Name: 2',3'-di-O-acetyl-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl(S_R)>adenosine
• CAS No.: 121517-95-1
• Molecular Formula: C₂₁H₂₃N₅O₇S
• Molecular Weight: 489.509
• Mol file: 121517-95-1.mol

Synonyms:2',3'-di-O-acetyl-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl(S_R)>adenosine

Chemical Property of 2',3'-di-O-acetyl-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl(S_R)>adenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2',3'-di-O-acetyl-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl(S_R)>adenosine

There total 9 articles about 2',3'-di-O-acetyl-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl(S_R)>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: 67.0%

2',3'-di-O-acetyl-5'-chloro-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl(5'S,SS)>adenosine (144494-01-9) → 2',3'-di-O-acetyl-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl(SR)>adenosine (121517-95-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 5h; Heating;

DOI:10.1021/jo00053a022

Reference yield: 32.0%

2',3'-di-O-acetyl-5'-S-(4-methoxyphenyl)-5'-thioadenosine (144493-94-7) → 2',3'-di-O-acetyl-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl(SS)>adenosine (121517-96-2) + 2',3'-di-O-acetyl-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl(SR)>adenosine (121517-95-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -50 ℃;

DOI:10.1021/jo00053a022

Reference yield:

5'-S-(4-methoxyphenyl)-5'-thioadenosine (137103-06-1) → 2',3'-di-O-acetyl-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl(SR)>adenosine (121517-95-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / pyridine / 7 h / 0 °C

2: MCPBA / CH₂Cl₂ / -40 °C

With pyridine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jo00082a010

upstream raw materials:

acetic anhydride

5'-S-(4-methoxyphenyl)-5'-thioadenosine

4-Methoxybenzenethiol

5'-deoxy-5'-chloroadenosine

Downstream raw materials:

5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl(S_S)>adenosine

5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl(S_R)>adenosine

2',3'-di-O-acetyl-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl(S_S)>adenosine

5'-Fluoro-5'-S-(4-methoxyphenyl)-5'-thioadenosine