1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-ethyluracil

Base Information

• Chemical Name: 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-ethyluracil
• CAS No.: 171721-04-3
• Molecular Formula: C₂₅H₂₃FN₂O₇
• Molecular Weight: 482.465
• Mol file: 171721-04-3.mol

Synonyms:

Chemical Property of 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-ethyluracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-ethyluracil

There total 13 articles about 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-ethyluracil 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:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose (3080-30-6,6974-32-9,14215-97-5,16162-35-9,20822-87-1,21138-42-1,22249-15-6,22249-17-8,26287-72-9,53403-35-3,53403-36-4,57236-69-8,70832-64-3,99395-04-7,100101-51-7,109668-83-9,120019-54-7) → 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-ethyluracil (171721-04-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) HCl(g), AcCl, 2.) H₂O / 1.) CH₂Cl₂, 0 deg C, 2.) CH₃CN

2: 1.) SO₂Cl₂ / 1.) CH₂Cl₂, DMF, from -40 deg C to RT, 3.5 h, 2.) CH₂Cl₂, DMF, RT, 15 h

3: 65 percent / KHF₂, 48percent aq. HF / various solvent(s) / 1 h / 160 °C

4: 100 percent / HBr, AcOH / CH₂Cl₂ / 20 h / Ambient temperature

5: 1.) HMDS, (NH₄)2SO₄ / 2.) dichloroethane, reflux, 20 h

With hydrogenchloride; ammonium sulfate; sulfuryl dichloride; potassium hydrogen bifluoride; hydrogen fluoride; water; hydrogen bromide; acetic acid; acetyl chloride; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane;

DOI:10.1021/jm960098l

Reference yield:

benzoyl chloride (98-88-4) → 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-ethyluracil (171721-04-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / pyridine / 3 h / Ambient temperature

2: 1percent HCl / methanol / 30 h / Ambient temperature

3: pyridine / 3 h / Ambient temperature

4: AcOH, conc. H₂SO₄ / Ambient temperature

5: 1.) HCl(g), AcCl, 2.) H₂O / 1.) CH₂Cl₂, 0 deg C, 2.) CH₃CN

6: 1.) SO₂Cl₂ / 1.) CH₂Cl₂, DMF, from -40 deg C to RT, 3.5 h, 2.) CH₂Cl₂, DMF, RT, 15 h

7: 65 percent / KHF₂, 48percent aq. HF / various solvent(s) / 1 h / 160 °C

8: 100 percent / HBr, AcOH / CH₂Cl₂ / 20 h / Ambient temperature

9: 1.) HMDS, (NH₄)2SO₄ / 2.) dichloroethane, reflux, 20 h

With pyridine; hydrogenchloride; ammonium sulfate; sulfuryl dichloride; potassium hydrogen bifluoride; sulfuric acid; hydrogen fluoride; water; hydrogen bromide; acetic acid; acetyl chloride; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; dichloromethane;

DOI:10.1021/jm960098l

Reference yield:

5-O-benzoyl-1,2-O-isopropylidene-α-L-erythro-pentofuranose-3-ulose (166411-40-1) → 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-ethyluracil (171721-04-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 79 percent / NaBH₄, H₂O / ethanol / 4 h / Ambient temperature

2: 98 percent / pyridine / 3 h / Ambient temperature

3: 1percent HCl / methanol / 30 h / Ambient temperature

4: pyridine / 3 h / Ambient temperature

5: AcOH, conc. H₂SO₄ / Ambient temperature

6: 1.) HCl(g), AcCl, 2.) H₂O / 1.) CH₂Cl₂, 0 deg C, 2.) CH₃CN

7: 1.) SO₂Cl₂ / 1.) CH₂Cl₂, DMF, from -40 deg C to RT, 3.5 h, 2.) CH₂Cl₂, DMF, RT, 15 h

8: 65 percent / KHF₂, 48percent aq. HF / various solvent(s) / 1 h / 160 °C

9: 100 percent / HBr, AcOH / CH₂Cl₂ / 20 h / Ambient temperature

10: 1.) HMDS, (NH₄)2SO₄ / 2.) dichloroethane, reflux, 20 h

With pyridine; hydrogenchloride; ammonium sulfate; sodium tetrahydroborate; sulfuryl dichloride; potassium hydrogen bifluoride; sulfuric acid; hydrogen fluoride; water; hydrogen bromide; acetic acid; acetyl chloride; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; ethanol; dichloromethane;

DOI:10.1021/jm960098l

upstream raw materials:

5-ethyluracil

1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose

1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose

benzoyl chloride

Refernces