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

Base Information

• Chemical Name: 9-[2-deoxy-2-methoxalylamino-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-N⁶-benzoyladenine
• CAS No.: 1006062-22-1
• Molecular Formula: C₄₁H₃₈N₆O₉
• Molecular Weight: 758.788

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

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

Chemical Property:

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

There total 5 articles about 9-[2-deoxy-2-methoxalylamino-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-N⁶-benzoyladenine 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: 44.0%

Dimethyl oxalate (553-90-2) + 9-[2-amino-2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-N6-benzoyladenine (1006062-20-9) → 9-[2-deoxy-2-methoxalylamino-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-N6-benzoyladenine (1006062-22-1)

Guidance literature:

With triethylamine; In methanol; at 20 ℃; for 14h;

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

Reference yield:

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

Guidance literature:

Multi-step reaction with 3 steps

1: 70 mg / pyridine; 4-(dimethylamino)pyridine / 16 h

2: 87 percent / hydrogen; aq. NH₃ / Pd/C / dioxane; H₂O / 12 h / atmospheric pressure

3: 44 percent / triethylamine / methanol / 14 h / 20 °C

With pyridine; dmap; ammonium hydroxide; hydrogen; triethylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; water;

DOI:10.1007/s11172-006-0473-y

upstream raw materials:

Dimethyl oxalate

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

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

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

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