(2R,3R,4R,5R)-2-((6-amino-5-nitropyrimidin-4-yl)amino)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-((6-amino-5-nitropyrimidin-4-yl)amino)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate
• CAS No.: 112220-31-2
• Molecular Formula: C₃₀H₂₅N₅O₉
• Molecular Weight: 599.557
• Mol file: 112220-31-2.mol

Synonyms:(2R,3R,4R,5R)-2-((6-amino-5-nitropyrimidin-4-yl)amino)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate

Chemical Property of (2R,3R,4R,5R)-2-((6-amino-5-nitropyrimidin-4-yl)amino)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R)-2-((6-amino-5-nitropyrimidin-4-yl)amino)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate

There total 5 articles about (2R,3R,4R,5R)-2-((6-amino-5-nitropyrimidin-4-yl)amino)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate 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: 92.0%

4,6-Diamino-5-nitropyrimidine (2164-84-3) + 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (14215-97-5) → (2R,3R,4R,5R)-2-((6-amino-5-nitropyrimidin-4-yl)amino)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate (112220-31-2)

Guidance literature:

4,6-Diamino-5-nitropyrimidine; With trimethylsilyl trifluoromethanesulfonate; triethylamine; In acetonitrile; at 20 ℃; for 1h;

1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose; In acetonitrile; at 20 ℃; for 16h;

DOI:10.1021/acs.joc.7b00780

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + 4,6-Diamino-5-nitropyrimidine (2164-84-3) → (2R,3R,4R,5R)-2-((6-amino-5-nitropyrimidin-4-yl)amino)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate (112220-31-2)

Guidance literature:

With pyridine; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; 1,1,1,3,3,3-hexamethyl-disilazane; Yield given. Multistep reaction; 1.) reflux, 16 h, 2.) CH₃CN, 18 h;

DOI:10.1021/jm00399a017

Reference yield:

β-D-ribofuranose 5-t-butyldiphenylsilyloxy-2,3,5-tribenzoate (651013-63-7) → (2R,3R,4R,5R)-2-((6-amino-5-nitropyrimidin-4-yl)amino)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate (112220-31-2)

Guidance literature:

4,6-Diamino-5-nitropyrimidine; With pyridine; ammonium sulfate; sulfuric acid; In hexamethyldisilazan; for 1.5h; Heating / reflux;

β-D-ribofuranose 5-t-butyldiphenylsilyloxy-2,3,5-tribenzoate; With trimethylsilyl trifluoromethanesulfonate; In hexamethyldisilazan; acetonitrile; at 20 ℃; for 4.5h;

upstream raw materials:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

4,6-Diamino-5-nitropyrimidine

C₃₀H₂₅N₅O₉

β-D-ribofuranose 5-t-butyldiphenylsilyloxy-2,3,5-tribenzoate

Downstream raw materials:

Clitocine