N⁴-dibenzoylamino-N⁷-benzoylamino-1-(2-deoxy-β-D-ribofuranosyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine

Base Information

• Chemical Name: N⁴-dibenzoylamino-N⁷-benzoylamino-1-(2-deoxy-β-D-ribofuranosyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine
• CAS No.: 597551-59-2
• Molecular Formula: C₃₄H₂₇N₇O₆
• Molecular Weight: 629.632

Synonyms:N⁴-dibenzoylamino-N⁷-benzoylamino-1-(2-deoxy-β-D-ribofuranosyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine

Chemical Property of N⁴-dibenzoylamino-N⁷-benzoylamino-1-(2-deoxy-β-D-ribofuranosyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine

Chemical Property:

Purity/Quality:

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Technology Process of N⁴-dibenzoylamino-N⁷-benzoylamino-1-(2-deoxy-β-D-ribofuranosyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine

There total 7 articles about N⁴-dibenzoylamino-N⁷-benzoylamino-1-(2-deoxy-β-D-ribofuranosyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine 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: 100.0%

N4-dibenzoylamino-N7-benzoylamino-1-(2-deoxy-3,5-di-O-triisopropylsilyl-β-D-ribofuranosyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine (597551-58-1) → N4-dibenzoylamino-N7-benzoylamino-1-(2-deoxy-β-D-ribofuranosyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine (597551-59-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1021/ja0347686

Reference yield:

5-amino-1-(2-deoxy-3,5-di-O-triisopropylsilyl-β-D-ribofuranosyl)imidazole-4-carbonitrile (597551-53-6) → N4-dibenzoylamino-N7-benzoylamino-1-(2-deoxy-β-D-ribofuranosyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine (597551-59-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 57 percent / diiodomethane; isoamyl nitrite / CHCl₃ / Heating

2.1: dba3Pd₂*CHCl₃ / dimethylformamide / 11 h / 100 °C

2.2: 69 percent / Na₂CO₃ / aq. ethanol / 1 h / 80 °C

3.1: 86 percent / NH₄OH / dioxane / 24 h / 100 °C

4.1: 71 percent / pyridine / 4.5 h / 20 °C

5.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; ammonium hydroxide; diiodomethane; tetrabutyl ammonium fluoride; isopentyl nitrite; In tetrahydrofuran; 1,4-dioxane; chloroform; N,N-dimethyl-formamide; 2.1: Stille coupling;

DOI:10.1021/ja0347686

Reference yield:

1-(2-deoxy-3,5-di-O-triisopropylsilyl-β-D-ribofuranosyl)-5-iodoimidazole-4-carbonitrile (597551-55-8) → N4-dibenzoylamino-N7-benzoylamino-1-(2-deoxy-β-D-ribofuranosyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine (597551-59-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dba3Pd₂*CHCl₃ / dimethylformamide / 11 h / 100 °C

1.2: 69 percent / Na₂CO₃ / aq. ethanol / 1 h / 80 °C

2.1: 86 percent / NH₄OH / dioxane / 24 h / 100 °C

3.1: 71 percent / pyridine / 4.5 h / 20 °C

4.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; ammonium hydroxide; tetrabutyl ammonium fluoride; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; 1.1: Stille coupling;

DOI:10.1021/ja0347686

upstream raw materials:

N⁴-dibenzoylamino-N⁷-benzoylamino-1-(2-deoxy-3,5-di-O-triisopropylsilyl-β-D-ribofuranosyl)imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine

1-(2-deoxy-3,5-di-O-triisopropylsilyl-β-D-ribofuranosyl)-5-iodoimidazole-4-carbonitrile

5-amino-1-(2-deoxy-3,5-di-O-triisopropylsilyl-β-D-ribofuranosyl)imidazole-4-carbonitrile

5-amino-1-(2-deoxy-3,5-di-O-triisopropylsilyl-β-D-ribofuranosyl)imidazole-4-carboxamide

Downstream raw materials:

N⁴-dibenzoylamino-N⁷-benzoylamino-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine

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