9-<2-azido-2,3-dideoxy-5-(methylcarbamoyl)-β-D-arabinofuranosyl>-2-chloro-N⁶-(3-iodobenzyl)adenine

Base Information

• Chemical Name: 9-<2-azido-2,3-dideoxy-5-(methylcarbamoyl)-β-D-arabinofuranosyl>-2-chloro-N⁶-(3-iodobenzyl)adenine
• CAS No.: 163042-82-8
• Molecular Formula: C₁₈H₁₇ClIN₉O₂
• Molecular Weight: 553.75

Synonyms:9-<2-azido-2,3-dideoxy-5-(methylcarbamoyl)-β-D-arabinofuranosyl>-2-chloro-N⁶-(3-iodobenzyl)adenine

Chemical Property of 9-<2-azido-2,3-dideoxy-5-(methylcarbamoyl)-β-D-arabinofuranosyl>-2-chloro-N⁶-(3-iodobenzyl)adenine

Chemical Property:

Purity/Quality:

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Technology Process of 9-<2-azido-2,3-dideoxy-5-(methylcarbamoyl)-β-D-arabinofuranosyl>-2-chloro-N⁶-(3-iodobenzyl)adenine

There total 7 articles about 9-<2-azido-2,3-dideoxy-5-(methylcarbamoyl)-β-D-arabinofuranosyl>-2-chloro-N⁶-(3-iodobenzyl)adenine 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: 34.0%

2-chloro-9-<3-deoxy-2-(methylsulfonyl)-5-(methylcarbamoyl)-β-D-ribofuranosyl>-N6-(3-iodobenzyl)adenine (163042-86-2) → 9-<2-azido-2,3-dideoxy-5-(methylcarbamoyl)-β-D-arabinofuranosyl>-2-chloro-N6-(3-iodobenzyl)adenine (163042-82-8)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 100 ℃; for 41h;

DOI:10.1021/jm00010a017

Reference yield:

3-iodobenzylamine hydrochloride (3718-88-5) → 9-<2-azido-2,3-dideoxy-5-(methylcarbamoyl)-β-D-arabinofuranosyl>-2-chloro-N6-(3-iodobenzyl)adenine (163042-82-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 57 percent / triethylamine / ethanol / 120 h / Ambient temperature

2: ammonium sulfate / 2 h / Heating

3: TMS triflate / 1,2-dichloro-ethane / 17 h / 90 °C

4: 43 percent / NH₃ / methanol / 18 h / Ambient temperature

5: 78 percent / pyridine / CH₂Cl₂ / 1.5 h / Ambient temperature

6: 34 percent / sodium azide / dimethylformamide / 41 h / 100 °C

With pyridine; ammonium sulfate; sodium azide; trimethylsilyl trifluoromethanesulfonate; ammonia; triethylamine; In methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00010a017

Reference yield:

2,6 dichloropurine (5451-40-1) → 9-<2-azido-2,3-dideoxy-5-(methylcarbamoyl)-β-D-arabinofuranosyl>-2-chloro-N6-(3-iodobenzyl)adenine (163042-82-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 57 percent / triethylamine / ethanol / 120 h / Ambient temperature

2: ammonium sulfate / 2 h / Heating

3: TMS triflate / 1,2-dichloro-ethane / 17 h / 90 °C

4: 43 percent / NH₃ / methanol / 18 h / Ambient temperature

5: 78 percent / pyridine / CH₂Cl₂ / 1.5 h / Ambient temperature

6: 34 percent / sodium azide / dimethylformamide / 41 h / 100 °C

With pyridine; ammonium sulfate; sodium azide; trimethylsilyl trifluoromethanesulfonate; ammonia; triethylamine; In methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00010a017

upstream raw materials:

2-chloro-9-<3-deoxy-2-(methylsulfonyl)-5-(methylcarbamoyl)-β-D-ribofuranosyl>-N⁶-(3-iodobenzyl)adenine

3-iodobenzylamine hydrochloride

2,6 dichloropurine

2-chloro-N-⁶-(3-iodobenzyl)adenine

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