Benzoic acid (2S,4S,5R)-4-fluoro-5-purin-9-yl-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2S,4S,5R)-4-fluoro-5-purin-9-yl-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 1027658-35-0
• Molecular Formula: C₁₇H₁₅FN₄O₃
• Molecular Weight: 342.33
• Mol file: 1027658-35-0.mol

Synonyms:Benzoic acid (2S,4S,5R)-4-fluoro-5-purin-9-yl-tetrahydro-furan-2-ylmethyl ester

Chemical Property of Benzoic acid (2S,4S,5R)-4-fluoro-5-purin-9-yl-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,4S,5R)-4-fluoro-5-purin-9-yl-tetrahydro-furan-2-ylmethyl ester

There total 6 articles about Benzoic acid (2S,4S,5R)-4-fluoro-5-purin-9-yl-tetrahydro-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:

6-Chloro-9-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)-9H-purine (135473-20-0) → Benzoic acid (2S,4S,5R)-4-fluoro-5-purin-9-yl-tetrahydro-furan-2-ylmethyl ester (1027658-35-0)

Guidance literature:

With ammonium hydroxide; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; for 3h; under 2585.7 Torr; Ambient temperature;

DOI:10.1021/jm00032a017

Reference yield:

[(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate (4105-29-7) → Benzoic acid (2S,4S,5R)-4-fluoro-5-purin-9-yl-tetrahydro-furan-2-ylmethyl ester (1027658-35-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / H₂SO₄ / H₂O; dioxane / 4 h / 70 - 80 °C

2: 49.8 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 0 - 25 °C

3: 20 percent / TMSOTf / 1,2-dichloro-ethane / Heating

4: H₂, NH₄OH / 10percent Pd/C / methanol; tetrahydrofuran / 3 h / 2585.7 Torr / Ambient temperature

With ammonium hydroxide; diethylamino-sulfur trifluoride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; hydrogen; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 1,2-dichloro-ethane;

DOI:10.1021/jm00032a017

Reference yield:

5-O-benzoyl-3-deoxy-D-ribofuranose → Benzoic acid (2S,4S,5R)-4-fluoro-5-purin-9-yl-tetrahydro-furan-2-ylmethyl ester (1027658-35-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 49.8 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 0 - 25 °C

2: 20 percent / TMSOTf / 1,2-dichloro-ethane / Heating

3: H₂, NH₄OH / 10percent Pd/C / methanol; tetrahydrofuran / 3 h / 2585.7 Torr / Ambient temperature

With ammonium hydroxide; diethylamino-sulfur trifluoride; trimethylsilyl trifluoromethanesulfonate; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/jm00032a017

upstream raw materials:

6-Chloro-9-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)-9H-purine

6-chloro-9-trimethylsilylpurine

[(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate

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

Downstream raw materials:

9-(2',3'-dideoxy-2'-fluoro-β-D-arabinofuranosyl)-9H-purine

Refernces