[5-[2,4-Dioxo-5-(trifluoromethyl)pyrimidin-1-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate

Base Information

• Chemical Name: [5-[2,4-Dioxo-5-(trifluoromethyl)pyrimidin-1-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS No.: 7057-46-7
• Molecular Formula: C26H23F3N2O7
• Molecular Weight: 532.473
• NSC Number: 92421
• DSSTox Substance ID: DTXSID00990795
• Mol file: 7057-46-7.mol

Synonyms:[5-[2,4-dioxo-5-(trifluoromethyl)pyrimidin-1-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate;7057-46-7;NSC92421;DTXSID00990795;NSC-92421;1-[2-Deoxy-3,5-bis-O-(4-methylbenzoyl)pentofuranosyl]-4-hydroxy-5-(trifluoromethyl)pyrimidin-2(1H)-one

Chemical Property of [5-[2,4-Dioxo-5-(trifluoromethyl)pyrimidin-1-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 116.69000
• Density: 1.44g/cm³
• LogP: 3.54230
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 532.14573556
• Heavy Atom Count: 38
• Complexity: 953

Purity/Quality:

97% ^*data from raw suppliers

Thymidine,α,α,α-trifluoro-,3',5'-bis(4-methylbenzoate) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C(=O)OCC2C(CC(O2)N3C=C(C(=O)NC3=O)C(F)(F)F)OC(=O)C4=CC=C(C=C4)C

Technology Process of [5-[2,4-Dioxo-5-(trifluoromethyl)pyrimidin-1-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate

There total 2 articles about [5-[2,4-Dioxo-5-(trifluoromethyl)pyrimidin-1-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate 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: 68.0%

p-methylbenzoic anhydride (13222-85-0) + 2'-deoxy-5-trifluoromethyluridine (70-00-8) → (2R,3S,5R)-5-(2,4-dioxo-5-(trifluoromethyl)-3,4-dihydropyrimidin-1(2H)-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl-4-methylbenzoate (7057-46-7)

Guidance literature:

dmap; In acetonitrile;

DOI:10.1248/cpb.35.2090

Reference yield:

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) + 5-trifluoromethyluracil (54-20-6) → (2R,3S,5R)-5-(2,4-dioxo-5-(trifluoromethyl)-3,4-dihydropyrimidin-1(2H)-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl-4-methylbenzoate (7057-46-7)

Guidance literature:

5-trifluoromethyluracil; With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane; at 120 - 125 ℃; for 3h;

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride; With zinc(II) chloride; In dichloromethane; at 25 - 30 ℃; for 3h; Temperature;

Reference yield:

(2R,3S,5R)-5-(2,4-dioxo-5-(trifluoromethyl)-3,4-dihydropyrimidin-1(2H)-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl-4-methylbenzoate (7057-46-7) → 2'-deoxy-5-trifluoromethyluridine (70-00-8)

Guidance literature:

With methanol; sodium methylate; at 10 - 15 ℃; for 1.5h; Temperature;

upstream raw materials:

p-methylbenzoic anhydride

2'-deoxy-5-trifluoromethyluridine

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

5-trifluoromethyluracil

Downstream raw materials:

2'-deoxy-5-trifluoromethyluridine

Refernces

• 1、 Yamashita,Takeda,Matsumoto,Terada,Unemi,Yasumoto. "Studies on antitumor agents. VI. Syntheses and antitumor activities of acyl derivatives of 2'-deoxy-5-trifluoromethyluridine.". . p. 2090 - 2094. Retrieved 2007/10/02.