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

Base Information

• Chemical Name: 1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)cytosine
• CAS No.: 119555-43-0
• Molecular Formula: C₁₆H₁₆FN₃O₄
• Molecular Weight: 333.319
• Mol file: 119555-43-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about 1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)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: 31.0%

O-benzoyl-2,3-dideoxy-2-fluoro-3-iodo-β-D-arabinofuranosyl)cytosine (119555-42-9) → (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) + 1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)cytosine (119555-43-0)

Guidance literature:

With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In water; for 19h; under 760 Torr; Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jm00170a015

Reference yield:

1-(5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)cytosine (119555-40-7) → 1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)cytosine (119555-43-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / pyridine / 18 h / 0 °C

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

3: 31 percent / NaHCO₃, H₂ / 10percent Pd/C / H₂O / 19 h / 760 Torr / Ambient temperature

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

DOI:10.1021/jm00170a015

Reference yield:

1-<5-O-benzoyl-2-deoxy-2-fluoro-3-O-(methylsulfonyl)-β-D-arabinofuranosyl>cytosine (119555-41-8) → 1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)cytosine (119555-43-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / NaI / butan-2-one / 18 h / Heating

2: 31 percent / NaHCO₃, H₂ / 10percent Pd/C / H₂O / 19 h / 760 Torr / Ambient temperature

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

DOI:10.1021/jm00170a015

upstream raw materials:

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

bis(trimethylsilyl)cytosine

5-O-benzoyl-2,3-dideoxy-2-fluoro-α-D-arabinofuranosyl bromide

2,4-O,N-bis(trimethylsilyl)cytosine

Downstream raw materials:

1-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)uracil

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

Refernces

• 1、 Wysocki Jr.,Siddiqui,Barchi Jr.,Driscoll,Marquez. "A more expedient approach to the synthesis of anti-HIV-active 2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl nucleosides". . p. 1005 - 1008. Retrieved 2007/10/02.