1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)cytosine

Base Information

• Chemical Name: 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)cytosine
• CAS No.: 69123-99-5
• Molecular Formula: C₁₈H₁₈FN₃O₆
• Molecular Weight: 391.356
• Mol file: 69123-99-5.mol

Synonyms:1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)cytosine

Chemical Property of 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)cytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)cytosine

There total 1 articles about 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)cytosine 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:

3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranosyl bromide (92283-83-5) + bis(trimethylsilyl)cytosine (67014-25-9) → 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)cytosine (69123-99-5) + Benzoic acid (2R,3R,4S,5S)-3-acetoxy-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-fluoro-tetrahydro-furan-2-ylmethyl ester (128496-22-0)

Guidance literature:

In chloroform; for 20h; Yield given. Yields of byproduct given; Heating;

DOI:10.1021/jm00170a015

Reference yield: 78.0%

1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)cytosine (69123-99-5) → 1-(5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)cytosine (119555-40-7)

Guidance literature:

With ammonia; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jm00170a015

Reference yield:

1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)cytosine (69123-99-5) → (5-O-benzoyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)cytosine (81252-62-2,81252-63-3,117248-88-1,117248-89-2,121154-62-9,121154-63-0,128778-62-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / NH₃ / methanol / 2 h / Ambient temperature

2: 76 percent / pyridine / 18 h / 0 °C

3: 61 percent / NaI / butan-2-one / 18 h / Heating

4: NaHCO₃, H₂ / 10percent Pd/C / H₂O / 19 h / 760 Torr / Ambient temperature

With ammonia; hydrogen; sodium hydrogencarbonate; sodium iodide; palladium on activated charcoal; In pyridine; methanol; water; butanone;

DOI:10.1021/jm00170a015

upstream raw materials:

3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranosyl bromide

bis(trimethylsilyl)cytosine

Downstream raw materials:

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

(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)cytosine

1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)cytosine

O-benzoyl-2,3-dideoxy-2-fluoro-3-iodo-β-D-arabinofuranosyl)cytosine