1-{5'-O-[bis(4-methoxyphenyl)phyenylmethyl]-β-D-ribofuranosyl}-N⁶(phenoxyacetyl)-1H-imidazo[4,5-c]pyridin-6-amine

Base Information

• Chemical Name: 1-{5'-O-[bis(4-methoxyphenyl)phyenylmethyl]-β-D-ribofuranosyl}-N⁶(phenoxyacetyl)-1H-imidazo[4,5-c]pyridin-6-amine
• CAS No.: 663616-72-6
• Molecular Formula: C₅₃H₄₇N₅O₁₀
• Molecular Weight: 913.984

Synonyms:1-{5'-O-[bis(4-methoxyphenyl)phyenylmethyl]-β-D-ribofuranosyl}-N⁶(phenoxyacetyl)-1H-imidazo[4,5-c]pyridin-6-amine

Chemical Property of 1-{5'-O-[bis(4-methoxyphenyl)phyenylmethyl]-β-D-ribofuranosyl}-N⁶(phenoxyacetyl)-1H-imidazo[4,5-c]pyridin-6-amine

Chemical Property:

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Technology Process of 1-{5'-O-[bis(4-methoxyphenyl)phyenylmethyl]-β-D-ribofuranosyl}-N⁶(phenoxyacetyl)-1H-imidazo[4,5-c]pyridin-6-amine

There total 6 articles about 1-{5'-O-[bis(4-methoxyphenyl)phyenylmethyl]-β-D-ribofuranosyl}-N⁶(phenoxyacetyl)-1H-imidazo[4,5-c]pyridin-6-amine 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: 61.0%

diphenylcarbamic chloride (83-01-2) + 1-{5'-O-[bis(4-methoxyphenyl)phyenylmethyl]-β-D-ribofuranosyl}-1,5-dihydro-6-[(phenoxyacetyl)amino]-4H-imidazo[4,5-c]pyridin-4-one (663616-70-4) → 1-{5'-O-[bis(4-methoxyphenyl)phyenylmethyl]-β-D-ribofuranosyl}-N6(phenoxyacetyl)-1H-imidazo[4,5-c]pyridin-6-amine (663616-72-6) + 1-{5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-(diphenylcarbamoyl)-β-D-ribofuranosyl}-4-[(diphenylcarbamoyl)oxy]-N6(phenoxyacetyl)-1H-imidazo[4,5-c]pyridin-6-amine

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In pyridine; at 20 ℃; for 4h;

DOI:10.1002/hlca.200390222

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → 1-{5'-O-[bis(4-methoxyphenyl)phyenylmethyl]-β-D-ribofuranosyl}-N6(phenoxyacetyl)-1H-imidazo[4,5-c]pyridin-6-amine (663616-72-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hexamethyldisilazane; (NH₄)2SO₄ / 3 h / Heating

1.2: 92 percent / SnCl₄ / acetonitrile / 3 h / 20 °C

2.1: 70 percent / NH₃ / methanol / 48 h / 120 °C

3.1: 1,1,1,3,3,3-hexamethyldisilazane / dimethylformamide / 0.5 h / 20 °C

3.2: pyridine / 3 h

3.3: 72 percent / pyridine; H₂O / 0.25 h / 0 °C

4.1: 72 percent / pyridine / 4 h / 20 °C

5.1: 61 percent / (i-Pr)2EtN / pyridine / 4 h / 20 °C

With pyridine; ammonium sulfate; ammonia; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In pyridine; methanol; N,N-dimethyl-formamide; 1.2: Vorbrueggen glycosylation;

DOI:10.1002/hlca.200390222

Reference yield:

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-imidazo[4,5-c]pyridin-4(5H)-one (22566-91-2) → 1-{5'-O-[bis(4-methoxyphenyl)phyenylmethyl]-β-D-ribofuranosyl}-N6(phenoxyacetyl)-1H-imidazo[4,5-c]pyridin-6-amine (663616-72-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,1,1,3,3,3-hexamethyldisilazane / dimethylformamide / 0.5 h / 20 °C

1.2: pyridine / 3 h

1.3: 72 percent / pyridine; H₂O / 0.25 h / 0 °C

2.1: 72 percent / pyridine / 4 h / 20 °C

3.1: 61 percent / (i-Pr)2EtN / pyridine / 4 h / 20 °C

With pyridine; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In pyridine; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200390222

upstream raw materials:

diphenylcarbamic chloride

1-{5'-O-[bis(4-methoxyphenyl)phyenylmethyl]-β-D-ribofuranosyl}-1,5-dihydro-6-[(phenoxyacetyl)amino]-4H-imidazo[4,5-c]pyridin-4-one

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

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-imidazo[4,5-c]pyridin-4(5H)-one

Downstream raw materials:

1-{5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[tris(1-methylethyl)silyl]-β-D-ribofuranosyl}-4-[(diphenylcarbamoyl)oxy]-N⁶(phenoxyacetyl)-1H-imidazo[4,5-c]pyridin-6-amine

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