2,N⁶-dimethyl-N⁶-benzoyl-9-<5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-fluoro-β-D-arabinofuranosyl>adenine

Base Information

• Chemical Name: 2,N⁶-dimethyl-N⁶-benzoyl-9-<5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-fluoro-β-D-arabinofuranosyl>adenine
• CAS No.: 132722-96-4
• Molecular Formula: C₂₅H₃₄FN₅O₃Si
• Molecular Weight: 499.661

Synonyms:2,N⁶-dimethyl-N⁶-benzoyl-9-<5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-fluoro-β-D-arabinofuranosyl>adenine

Chemical Property of 2,N⁶-dimethyl-N⁶-benzoyl-9-<5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-fluoro-β-D-arabinofuranosyl>adenine

Chemical Property:

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Technology Process of 2,N⁶-dimethyl-N⁶-benzoyl-9-<5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-fluoro-β-D-arabinofuranosyl>adenine

There total 3 articles about 2,N⁶-dimethyl-N⁶-benzoyl-9-<5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-fluoro-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: 86.6%

2,N6-dimethyl-N6-benzoyl-9-<5'-O-(tert-butyldimethylsilyl)-3'-O-xanthyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl>adenine (132723-08-1) → 2,N6-dimethyl-N6-benzoyl-9-<5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-fluoro-β-D-arabinofuranosyl>adenine (132722-96-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 90 ℃; for 0.166667h;

DOI:10.1021/jm00109a018

Reference yield:

2-methyl-9-<5'-O-(tert-butyldimethylsilyl)-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl>adenine (132723-06-9) → 2,N6-dimethyl-N6-benzoyl-9-<5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-fluoro-β-D-arabinofuranosyl>adenine (132722-96-4)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 2 h / 0 °C

2: 2 N NaOH / 0.5 h / 0 °C

3: 1.) sodium hydride / 1.) DMF, 0 deg C, 30 min, 2.) DMF, 0 deg C, 20 min

4: 86.6 percent / AIBN, tri-n-butyltin hydride / toluene / 0.17 h / 90 °C

With pyridine; sodium hydroxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; In toluene;

DOI:10.1021/jm00109a018

Reference yield:

N-Benzoyl-N-{9-[(2R,3S,4R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-fluoro-4-hydroxy-tetrahydro-furan-2-yl]-2-methyl-9H-purin-6-yl}-benzamide → 2,N6-dimethyl-N6-benzoyl-9-<5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-fluoro-β-D-arabinofuranosyl>adenine (132722-96-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 2 N NaOH / 0.5 h / 0 °C

2: 1.) sodium hydride / 1.) DMF, 0 deg C, 30 min, 2.) DMF, 0 deg C, 20 min

3: 86.6 percent / AIBN, tri-n-butyltin hydride / toluene / 0.17 h / 90 °C

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; In toluene;

DOI:10.1021/jm00109a018

upstream raw materials:

2,N⁶-dimethyl-N⁶-benzoyl-9-<5'-O-(tert-butyldimethylsilyl)-3'-O-xanthyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl>adenine

2-methyl-9-<5'-O-(tert-butyldimethylsilyl)-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl>adenine

Downstream raw materials:

2,N⁶-dimethyl-9-(2',3'-dideoxy-2'-fluoro-β-D-arabinofuranosyl)adenine

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