1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-chlorouracil

Base Information

• Chemical Name: 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-chlorouracil
• CAS No.: 1321580-95-3
• Molecular Formula: C₂₃H₁₇ClF₂N₂O₇
• Molecular Weight: 506.847
• Mol file: 1321580-95-3.mol

Synonyms:1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-chlorouracil

Chemical Property of 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-chlorouracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-chlorouracil

There total 7 articles about 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-chlorouracil 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:

5-chloro-2,4-bis-O-trimethylsilyluracil (58990-53-7) + 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose (134877-42-2,134877-43-3,122111-11-9) → 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-chlorouracil (1321580-95-3) + 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranos-1-yl)-5-chlorouracil

Guidance literature:

5-chloro-2,4-bis-O-trimethylsilyluracil; 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose; With trimethylsilyl trifluoromethanesulfonate; In 1,1-dichloroethane; at 90 - 100 ℃; for 10h; Inert atmosphere;

With sodium hydrogencarbonate; In 1,1-dichloroethane; water; at 20 ℃;

DOI:10.1016/j.bmc.2011.05.037

Reference yield:

3’,5’-di-O-benzoyl-2’-deoxy-2’,2’-difluoro-5-(hydroxymethyl)uridine → 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-chlorouracil (1321580-95-3)

Guidance literature:

With chloro-trimethyl-silane; for 16h; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.12.051

Reference yield:

(2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate (1173824-58-2,143157-25-9,143157-22-6) → 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-chlorouracil (1321580-95-3)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

2: 1,1,1,3,3,3-hexamethyl-disilazane; ammonium sulfate / dichloromethane / 16 h / Reflux; Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran; chloroform / 16 h / 0 °C / Inert atmosphere

4: chloro-trimethyl-silane / 16 h / Inert atmosphere

With ammonium sulfate; chloro-trimethyl-silane; tetrabutyl ammonium fluoride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; chloroform;

DOI:10.1016/j.tetlet.2014.12.051

upstream raw materials:

(2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate

5-chloro-2,4-bis-O-trimethylsilyluracil

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose

2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate

Downstream raw materials:

C₂₅H₂₅ClF₂N₃O₉P

Refernces

• 1、 Quintiliani, Maurizio,Persoons, Leentje,Solaroli, Nicola,Karlsson, Anna,Andrei, Graciela,Snoeck, Robert,Balzarini, Jan,McGuigan, Christopher. "Design, synthesis and biological evaluation of 2′-deoxy-2′, 2′-difluoro-5-halouridine phosphoramidate ProTides". experimental part. p. 4338 - 4345. Retrieved 2011/09/12.