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

Base Information

• Chemical Name: 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
• CAS No.: 100034-47-7
• Molecular Formula: C₂₆H₃₁N₅O₁₀S₂
• Molecular Weight: 637.692

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 12 articles about 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 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)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester (30747-23-0) → 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)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; dmap; N-Bromosuccinimide; ammonia; di(n-butyl)tin oxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; methanol; 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) → 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)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1248/cpb.37.298

Reference yield:

2-acetamido-6-ethoxy-9-(β-D-ribofuranosyl)-9H-purine (105166-09-4) → 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)

Guidance literature:

Multi-step reaction with 7 steps

1: 97.5 percent / ammonia / methanol / 24 h / 65 °C / in a sealed tube

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

3: H₂O; dimethylformamide / 24 h / Ambient temperature

4: DMAP, pyridine / 24 h / Heating

5: ammonia / methanol / 8 h / Ambient temperature

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

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

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

DOI:10.1248/cpb.37.298

upstream raw materials:

acetic anhydride

2-acetamido-6-ethoxy-8-methylthio-9-(2-O-tosyl-1-β-D-ribofuranosyl)-9H-purine

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

Downstream raw materials:

2'-deoxy-8,2'-methanoguanosine

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

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