2'-DEOXY-3',5'-DI-O-(4-METHYLBENZOYL)-5-ETHYLURIDINE

Base Information

• Chemical Name: 2'-DEOXY-3',5'-DI-O-(4-METHYLBENZOYL)-5-ETHYLURIDINE
• CAS No.: 29900-44-5
• Molecular Formula: C27H28 N2 O7
• Molecular Weight: 492.52
• Mol file: 29900-44-5.mol

Synonyms:Uridine,2'-deoxy-5-ethyl-, 3',5'-di-p-toluate (8CI); p-Toluic acid, 3',5'-diester with2'-deoxy-5-ethyluridine (8CI)

Chemical Property of 2'-DEOXY-3',5'-DI-O-(4-METHYLBENZOYL)-5-ETHYLURIDINE

Chemical Property:

• PKA: 9.54±0.10(Predicted)
• PSA: 116.69000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: 3.08590

Purity/Quality:

97% ^*data from raw suppliers

2'-DEOXY-3',5'-DI-O-(4-METHYLBENZOYL)-5-ETHYLURIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2'-DEOXY-3',5'-DI-O-(4-METHYLBENZOYL)-5-ETHYLURIDINE

There total 8 articles about 2'-DEOXY-3',5'-DI-O-(4-METHYLBENZOYL)-5-ETHYLURIDINE 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: 67.0%

1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-ribofuranosyl)-4-trimethylsilyloxy-5-ethyl-2,4(1H,3H)-pyrimidinedione (78103-19-2) → 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-ribofuranosyl)-5-ethyl-2,4(1H,3H)-pyrimidinedione (29900-44-5) + 1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-ribofuranosyl)-5-ethyl-2,4(1H,3H)-pyrimidinedione (29900-45-6)

Guidance literature:

trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; acetonitrile; at 24 ℃; for 46h;

Reference yield: 31.5%

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) + 2,4-bis-trimethylsilyloxy-5-ethylpyrimidine (31167-05-2) → 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-ribofuranosyl)-5-ethyl-2,4(1H,3H)-pyrimidinedione (29900-44-5) + 1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-ribofuranosyl)-5-ethyl-2,4(1H,3H)-pyrimidinedione (29900-45-6)

Guidance literature:

trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; acetonitrile; at 24 ℃; for 3h;

Reference yield: 21.0%

5-ethyluracil (4212-49-1) + methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose (4330-34-1) → 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-ribofuranosyl)-5-ethyl-2,4(1H,3H)-pyrimidinedione (29900-44-5) + 1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-ribofuranosyl)-5-ethyl-2,4(1H,3H)-pyrimidinedione (29900-45-6)

Guidance literature:

With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane; C₄F₉SO₃K; In acetonitrile; for 12h; Heating;

upstream raw materials:

5-ethyluracil

methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose

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

2,4-bis-trimethylsilyloxy-5-ethylpyrimidine

Refernces

• 1、 Vorbrueggen, Helmut,Krolikiewicz, Konrad,Bennua, Baerbel. "Nucleoside Syntheses, XXII. Nucleoside Synthesis with Trimethylsilyl Triflate and Perchlorate as Catalysts". . p. 1234 - 1255. Retrieved 2007/10/02.