1-[2-(benzyloxycarbonyl)amino-2-deoxy-β-D-ribofuranosyl]uracil

Base Information

• Chemical Name: 1-[2-(benzyloxycarbonyl)amino-2-deoxy-β-D-ribofuranosyl]uracil
• CAS No.: 182626-48-8
• Molecular Formula: C₁₇H₁₉N₃O₇
• Molecular Weight: 377.354
• Mol file: 182626-48-8.mol

Synonyms:1-[2-(benzyloxycarbonyl)amino-2-deoxy-β-D-ribofuranosyl]uracil

Chemical Property of 1-[2-(benzyloxycarbonyl)amino-2-deoxy-β-D-ribofuranosyl]uracil

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[2-(benzyloxycarbonyl)amino-2-deoxy-β-D-ribofuranosyl]uracil

There total 1 articles about 1-[2-(benzyloxycarbonyl)amino-2-deoxy-β-D-ribofuranosyl]uracil 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: 52.0%

benzyl chloroformate (501-53-1,94274-21-2) + 1-(2-amino-2-deoxy-β-D-ribofuranosyl)uracil (26889-39-4,56888-92-7,68115-81-1) → 1-[2-(benzyloxycarbonyl)amino-2-deoxy-β-D-ribofuranosyl]uracil (182626-48-8)

Guidance literature:

With sodium hydrogencarbonate; In water; at 50 ℃; for 1h; pH=9;

DOI:10.1007/s11172-006-0473-y

Reference yield:

1-[2-(benzyloxycarbonyl)amino-2-deoxy-β-D-ribofuranosyl]uracil (182626-48-8) → 9-[2-amino-2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-N6-benzoyladenine (1006062-20-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: bis(trimethylsilyl)acetamide; CF₃SO₂OSiMe₃ / 1,2-dichloro-ethane

1.2: tetra(n-butyl)ammonium fluoride / dioxane / 1 h / 20 °C

2.1: 70 mg / pyridine; 4-(dimethylamino)pyridine / 16 h

3.1: 87 percent / hydrogen; aq. NH₃ / Pd/C / dioxane; H₂O / 12 h / atmospheric pressure

With pyridine; dmap; ammonium hydroxide; trimethylsilyl trifluoromethanesulfonate; hydrogen; bis-(trimethylsilyl)acetamide; palladium on activated charcoal; In 1,4-dioxane; water; 1,2-dichloro-ethane;

DOI:10.1007/s11172-006-0473-y

Reference yield:

1-[2-(benzyloxycarbonyl)amino-2-deoxy-β-D-ribofuranosyl]uracil (182626-48-8) → 9-[2-deoxy-2-methoxalylamino-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-N6-benzoyladenine (1006062-22-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: bis(trimethylsilyl)acetamide; CF₃SO₂OSiMe₃ / 1,2-dichloro-ethane

1.2: tetra(n-butyl)ammonium fluoride / dioxane / 1 h / 20 °C

2.1: 70 mg / pyridine; 4-(dimethylamino)pyridine / 16 h

3.1: 87 percent / hydrogen; aq. NH₃ / Pd/C / dioxane; H₂O / 12 h / atmospheric pressure

4.1: 44 percent / triethylamine / methanol / 14 h / 20 °C

With pyridine; dmap; ammonium hydroxide; trimethylsilyl trifluoromethanesulfonate; hydrogen; bis-(trimethylsilyl)acetamide; triethylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; water; 1,2-dichloro-ethane;

DOI:10.1007/s11172-006-0473-y

upstream raw materials:

benzyl chloroformate

1-(2-amino-2-deoxy-β-D-ribofuranosyl)uracil

Downstream raw materials:

9-[2-(benzyloxycarbonyl)amino-2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-N⁶-benzoyladenine

9-[2-amino-2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-N⁶-benzoyladenine

9-[2-deoxy-2-methoxalylamino-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-N⁶-benzoyladenine