1-<5-O-benzoyl-2-deoxy-2-fluoro-3-O-<(imidazol-1-yl)thiocarbonyl>-β-D-arabinofuranosyl>-N⁴-benzoylcytosine

Base Information

• Chemical Name: 1-<5-O-benzoyl-2-deoxy-2-fluoro-3-O-<(imidazol-1-yl)thiocarbonyl>-β-D-arabinofuranosyl>-N⁴-benzoylcytosine
• CAS No.: 128115-06-0
• Molecular Formula: C₂₇H₂₂FN₅O₆S
• Molecular Weight: 563.566

Synonyms:1-<5-O-benzoyl-2-deoxy-2-fluoro-3-O-<(imidazol-1-yl)thiocarbonyl>-β-D-arabinofuranosyl>-N⁴-benzoylcytosine

Chemical Property of 1-<5-O-benzoyl-2-deoxy-2-fluoro-3-O-<(imidazol-1-yl)thiocarbonyl>-β-D-arabinofuranosyl>-N⁴-benzoylcytosine

Chemical Property:

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Technology Process of 1-<5-O-benzoyl-2-deoxy-2-fluoro-3-O-<(imidazol-1-yl)thiocarbonyl>-β-D-arabinofuranosyl>-N⁴-benzoylcytosine

There total 4 articles about 1-<5-O-benzoyl-2-deoxy-2-fluoro-3-O-<(imidazol-1-yl)thiocarbonyl>-β-D-arabinofuranosyl>-N⁴-benzoylcytosine 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: 78.0%

1-(5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-N4-benzoylcytosine (121353-94-4) + 1,1'-Thiocarbonyldiimidazole (6160-65-2) → 1-<5-O-benzoyl-2-deoxy-2-fluoro-3-O-<(imidazol-1-yl)thiocarbonyl>-β-D-arabinofuranosyl>-N4-benzoylcytosine (128115-06-0)

Guidance literature:

In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1021/jm00170a016

Reference yield:

fiacitabine (69123-90-6) → 1-<5-O-benzoyl-2-deoxy-2-fluoro-3-O-<(imidazol-1-yl)thiocarbonyl>-β-D-arabinofuranosyl>-N4-benzoylcytosine (128115-06-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / H₂, conc. aq. NH₄OH / 10percent Pd/C / ethanol / 2 h / 1034.3 Torr

2: 72 percent / pyridine / 0.5 h / Ambient temperature

3: 78 percent / dimethylformamide / Ambient temperature

With pyridine; ammonium hydroxide; hydrogen; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00170a016

Reference yield:

benzoyl chloride (98-88-4) → 1-<5-O-benzoyl-2-deoxy-2-fluoro-3-O-<(imidazol-1-yl)thiocarbonyl>-β-D-arabinofuranosyl>-N4-benzoylcytosine (128115-06-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / pyridine / 0.5 h / Ambient temperature

2: 78 percent / dimethylformamide / Ambient temperature

With pyridine; In N,N-dimethyl-formamide;

DOI:10.1021/jm00170a016

upstream raw materials:

1-(5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-N⁴-benzoylcytosine

1,1'-Thiocarbonyldiimidazole

benzoyl chloride

1-(2-fluoro-2-deoxy-β-D-arabinofuranosyl)cytosine

Downstream raw materials:

1-(2,3-Dideoxy-2-fluoro-β-D-arabinofuranosyl)-cytosine

1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl-N⁴-benzoylcytosine

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