5'-O-(p-toluenesulfonyl)-2',3'-O'-isopropylideneadenosine N¹-oxide

Base Information

• Chemical Name: 5'-O-(p-toluenesulfonyl)-2',3'-O'-isopropylideneadenosine N¹-oxide
• CAS No.: 72525-43-0
• Molecular Formula: C₂₀H₂₃N₅O₇S
• Molecular Weight: 477.498
• Mol file: 72525-43-0.mol

Synonyms:5'-O-(p-toluenesulfonyl)-2',3'-O'-isopropylideneadenosine N¹-oxide

Chemical Property of 5'-O-(p-toluenesulfonyl)-2',3'-O'-isopropylideneadenosine N¹-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5'-O-(p-toluenesulfonyl)-2',3'-O'-isopropylideneadenosine N¹-oxide

There total 1 articles about 5'-O-(p-toluenesulfonyl)-2',3'-O'-isopropylideneadenosine N¹-oxide 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: 81.0%

((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate (5605-63-0) → 5'-O-(p-toluenesulfonyl)-2',3'-O'-isopropylideneadenosine N1-oxide (72525-43-0)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In various solvent(s); at 2 - 3 ℃; for 24h;

DOI:10.1021/jo01293a005

Reference yield:

5'-O-(p-toluenesulfonyl)-2',3'-O'-isopropylideneadenosine N1-oxide (72525-43-0) → 5'-amino-5'-deoxy-2',3'-O-isopropylideneadenosine (21950-36-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 72.3 percent / LiN₃ / dimethylformamide / 2.25 h / 74 - 80 °C

2: H₂ / Ra-Ni / Ambient temperature; pressure

With lithium azide; hydrogen; Ra-Ni; In N,N-dimethyl-formamide;

DOI:10.1021/jo01293a005

Reference yield:

5'-O-(p-toluenesulfonyl)-2',3'-O'-isopropylideneadenosine N1-oxide (72525-43-0) → 5'-iodo-5'-deoxy-2',3'-O-isopropylideneadenosine (30685-66-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / NaI / acetone / 2.5 h / 80 - 85 °C

2: 56 percent / Si₂Cl₆ / CH₂Cl₂ / 0.75 h

With hexachlorodisilane; sodium iodide; In dichloromethane; acetone;

DOI:10.1021/jo01293a005

upstream raw materials:

((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate

Downstream raw materials:

5'-iodo-5'-deoxy-2',3'-O-isopropylideneadenosine

5'-amino-5'-deoxy-2',3'-O-isopropylideneadenosine

5'-azido-5'-deoxy-2',3'-O-isopropylidene adenosine