2-acetamido-6-ethoxy-8-methanesulfonyl-9-(3,5-di-O-acetyl-2-O-tosyl-1-β-D-ribofuranosyl)-9H-purine

Base Information

• Chemical Name: 2-acetamido-6-ethoxy-8-methanesulfonyl-9-(3,5-di-O-acetyl-2-O-tosyl-1-β-D-ribofuranosyl)-9H-purine
• CAS No.: 100034-48-8
• Molecular Formula: C₂₆H₃₁N₅O₁₂S₂
• Molecular Weight: 669.69
• Mol file: 100034-48-8.mol

Synonyms:

Chemical Property of 2-acetamido-6-ethoxy-8-methanesulfonyl-9-(3,5-di-O-acetyl-2-O-tosyl-1-β-D-ribofuranosyl)-9H-purine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-acetamido-6-ethoxy-8-methanesulfonyl-9-(3,5-di-O-acetyl-2-O-tosyl-1-β-D-ribofuranosyl)-9H-purine

There total 13 articles about 2-acetamido-6-ethoxy-8-methanesulfonyl-9-(3,5-di-O-acetyl-2-O-tosyl-1-β-D-ribofuranosyl)-9H-purine 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:

Acetic acid (2R,3R,4R,5R)-2-acetoxymethyl-5-(2-acetylamino-6-ethoxy-8-methylsulfanyl-purin-9-yl)-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-3-yl ester (100034-47-7) → 2-acetamido-6-ethoxy-8-methanesulfonyl-9-(3,5-di-O-acetyl-2-O-tosyl-1-β-D-ribofuranosyl)-9H-purine (100034-48-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 3h; Yield given; Ambient temperature;

DOI:10.1248/cpb.37.298

Reference yield:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester (30747-23-0) → 2-acetamido-6-ethoxy-8-methanesulfonyl-9-(3,5-di-O-acetyl-2-O-tosyl-1-β-D-ribofuranosyl)-9H-purine (100034-48-8)

Guidance literature:

Multi-step reaction with 10 steps

1: triphenylphosphine, diethyl azodicarboxylate / dioxane / 0.5 h / Ambient temperature

2: ammonia / methanol / Ambient temperature

3: 97.5 percent / ammonia / methanol / 24 h / 65 °C / in a sealed tube

4: 68.4 percent / NBS / dimethylformamide / 2 h / Ambient temperature

5: H₂O; dimethylformamide / 24 h / Ambient temperature

6: DMAP, pyridine / 24 h / Heating

7: ammonia / methanol / 8 h / Ambient temperature

8: 1.) dibutyltin oxide; 2.) triethylamine / 1.) methanol, reflux, 2 h; 2.) methanol, r.t., 3 h

9: triethylamine, DMAP / acetonitrile / 1 h / Ambient temperature

10: m-chloroperoxybenzoic acid / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; dmap; N-Bromosuccinimide; ammonia; di(n-butyl)tin oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1248/cpb.37.298

Reference yield:

2-amino-6-ethoxy-9-(β-D-ribofuranosyl)-9H-purine (39708-01-5) → 2-acetamido-6-ethoxy-8-methanesulfonyl-9-(3,5-di-O-acetyl-2-O-tosyl-1-β-D-ribofuranosyl)-9H-purine (100034-48-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 68.4 percent / NBS / dimethylformamide / 2 h / Ambient temperature

2: H₂O; dimethylformamide / 24 h / Ambient temperature

3: DMAP, pyridine / 24 h / Heating

4: ammonia / methanol / 8 h / Ambient temperature

5: 1.) dibutyltin oxide; 2.) triethylamine / 1.) methanol, reflux, 2 h; 2.) methanol, r.t., 3 h

6: triethylamine, DMAP / acetonitrile / 1 h / Ambient temperature

7: m-chloroperoxybenzoic acid / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; dmap; N-Bromosuccinimide; ammonia; di(n-butyl)tin oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1248/cpb.37.298

upstream raw materials:

Acetic acid (2R,3R,4R,5R)-2-acetoxymethyl-5-(2-acetylamino-6-ethoxy-8-methylsulfanyl-purin-9-yl)-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-3-yl ester

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester

2-amino-6-ethoxy-9-(β-D-ribofuranosyl)-9H-purine

2-acetamido-6-ethoxy-9-(β-D-ribofuranosyl)-9H-purine

Downstream raw materials:

2'-deoxy-8,2'-methanoguanosine

Refernces