Benzoic acid (2S,5R)-5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2S,5R)-5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester
• CAS No.: 219989-60-3
• Molecular Formula: C₁₆H₁₄FN₃O₄
• Molecular Weight: 331.303
• Mol file: 219989-60-3.mol

Synonyms:Benzoic acid (2S,5R)-5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester

Chemical Property of Benzoic acid (2S,5R)-5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,5R)-5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester

There total 6 articles about Benzoic acid (2S,5R)-5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester 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: 51.0%

C23H19FIN3O6 (219989-63-6) → Benzoic acid (2S,5R)-5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester (219989-60-3)

Guidance literature:

With acetic acid; zinc; In ethanol; ethyl acetate; at 70 ℃;

DOI:10.1016/S0960-894X(98)00599-X

Reference yield:

1,2-O-isopropylidene-3,5-di-O-benzoyl-α-D-xylofuranose (6893-67-0) → Benzoic acid (2S,5R)-5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester (219989-60-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 4 M H₂SO₄, 85percent AcOH / tetrahydrofuran / 60 °C

2: I₂, Ph₃P, imidazole / CH₂Cl₂ / Ambient temperature

3: NIS / 1,2-dichloro-ethane / Ambient temperature

4: 51 percent / Zn, AcOH / ethanol; ethyl acetate / 70 °C

With 1H-imidazole; N-iodo-succinimide; sulfuric acid; iodine; acetic acid; triphenylphosphine; zinc; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; 1,2-dichloro-ethane;

DOI:10.1016/S0960-894X(98)00599-X

Reference yield:

D-xylofuranose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → Benzoic acid (2S,5R)-5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester (219989-60-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / conc. H₂SO₄, acetone / Ambient temperature

2: pyridine / CH₂Cl₂ / 0 °C

3: 4 M H₂SO₄, 85percent AcOH / tetrahydrofuran / 60 °C

4: I₂, Ph₃P, imidazole / CH₂Cl₂ / Ambient temperature

5: NIS / 1,2-dichloro-ethane / Ambient temperature

6: 51 percent / Zn, AcOH / ethanol; ethyl acetate / 70 °C

With pyridine; 1H-imidazole; N-iodo-succinimide; sulfuric acid; iodine; acetic acid; triphenylphosphine; acetone; zinc; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; 1,2-dichloro-ethane;

DOI:10.1016/S0960-894X(98)00599-X

upstream raw materials:

C₂₃H₁₉FIN₃O₆

1,2-O-isopropylidene-3,5-di-O-benzoyl-α-D-xylofuranose

D-xylofuranose

1,2-O-isopropylidene-α-D-xylose

Downstream raw materials:

β-D-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine