9-[5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-3-O-(phenoxythiocarbonyl)-β-D-arabinofuranosyl]adenine

Base Information

• Chemical Name: 9-[5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-3-O-(phenoxythiocarbonyl)-β-D-arabinofuranosyl]adenine
• CAS No.: 125542-17-8
• Molecular Formula: C₂₃H₃₀FN₅O₄SSi
• Molecular Weight: 519.672
• Mol file: 125542-17-8.mol

Synonyms:9-[5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-3-O-(phenoxythiocarbonyl)-β-D-arabinofuranosyl]adenine

Chemical Property of 9-[5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-3-O-(phenoxythiocarbonyl)-β-D-arabinofuranosyl]adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-[5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-3-O-(phenoxythiocarbonyl)-β-D-arabinofuranosyl]adenine

There total 7 articles about 9-[5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-3-O-(phenoxythiocarbonyl)-β-D-arabinofuranosyl]adenine 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: 57.0%

6-amino-9-<5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-β-D-arabinofuranosyl>-9H-purine (111727-03-8) + phenylcarbonochloridothioate (1005-56-7) → 9-[5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-3-O-(phenoxythiocarbonyl)-β-D-arabinofuranosyl]adenine (125542-17-8)

Guidance literature:

With dmap; In acetonitrile; for 5h;

DOI:10.1021/jo020428b

Reference yield:

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine (20187-82-0,20227-41-2,64183-27-3,123334-75-8) → 9-[5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-3-O-(phenoxythiocarbonyl)-β-D-arabinofuranosyl]adenine (125542-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / imidazole / dimethylformamide

2: 57 percent / DMAP / acetonitrile / 5 h

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo020428b

Reference yield:

1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide (56632-81-6) → 9-[5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-3-O-(phenoxythiocarbonyl)-β-D-arabinofuranosyl]adenine (125542-17-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 4A molecular sieves / CH₂Cl₂ / 15 h / Heating

2: 90 percent / NH₃ / methanol / 84 h / 95 - 100 °C

3: 85 percent / imidazole / dimethylformamide / Ambient temperature

4: 0.029 g / (dimethylamido)pyridine / dimethylformamide; acetonitrile / 1.5 h / Ambient temperature

With 1H-imidazole; (dimethylamido)pyridine; 4 A molecular sieve; ammonia; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm00165a015

upstream raw materials:

6-amino-9-<5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-β-D-arabinofuranosyl>-9H-purine

phenylcarbonochloridothioate

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine

tert-butyldimethylsilyl chloride

Downstream raw materials:

iodenosine

2'-F-ara-ddI