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

Base Information

• Chemical Name: 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-bromouracil
• CAS No.: 1321580-94-2
• Molecular Formula: C₂₃H₁₇BrF₂N₂O₇
• Molecular Weight: 551.298
• Mol file: 1321580-94-2.mol

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

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

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-bromouracil

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

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) + 2,4-bis-(trimethylsilyloxy)-5-bromopyrimidine (33282-64-3) → 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-bromouracil (1321580-94-2) + 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranos-1-yl)-5-bromouracil

Guidance literature:

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose; 2,4-bis-(trimethylsilyloxy)-5-bromopyrimidine; 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:

(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-bromouracil (1321580-94-2) + 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranos-1-yl)-5-bromouracil

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / 1,1-dichloroethane / 10 h / 90 - 100 °C / Inert atmosphere

2.2: 20 °C

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In 1,1-dichloroethane; dichloromethane;

DOI:10.1016/j.bmc.2011.05.037

Reference yield:

2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate (122111-01-7,122111-02-8) → 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-bromouracil (1321580-94-2) + 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranos-1-yl)-5-bromouracil

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

3.1: trimethylsilyl trifluoromethanesulfonate / 1,1-dichloroethane / 10 h / 90 - 100 °C / Inert atmosphere

3.2: 20 °C

With trimethylsilyl trifluoromethanesulfonate; lithium tri-t-butoxyaluminum hydride; triethylamine; In tetrahydrofuran; diethyl ether; 1,1-dichloroethane; dichloromethane;

DOI:10.1016/j.bmc.2011.05.037

upstream raw materials:

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

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

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

2,4-bis-(trimethylsilyloxy)-5-bromopyrimidine

Downstream raw materials:

C₂₅H₂₅BrF₂N₃O₉P