9-(3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-N⁶-methyl-2-phenylethynyladenine

Base Information

• Chemical Name: 9-(3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-N⁶-methyl-2-phenylethynyladenine
• CAS No.: 879398-51-3
• Molecular Formula: C₂₀H₁₉N₉O₃
• Molecular Weight: 433.429

Synonyms:9-(3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-N⁶-methyl-2-phenylethynyladenine

Chemical Property of 9-(3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-N⁶-methyl-2-phenylethynyladenine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 9-(3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-N⁶-methyl-2-phenylethynyladenine

There total 5 articles about 9-(3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-N⁶-methyl-2-phenylethynyladenine 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:

2-iodo-N6-methyl-9-(tetrahydropyran-2-yl)adenine (879398-53-5) → 9-(3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-N6-methyl-2-phenylethynyladenine (879398-51-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / triethylamine; CuI / (PPh₃)2PdCl₂ / dimethylformamide / 3 h / 20 °C

2: 72 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

3: 24.4 percent / trimethylsilyl trifluoromethanesulfonate; N,O-bis(trimethylsilyl)acetamide / acetonitrile / 10 h / Heating

4: 91 percent / ammonia / methanol / 2 h / 20 °C

With copper(l) iodide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; ammonia; triethylamine; trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Sonogashira coupling;

DOI:10.1016/j.bmc.2005.09.062

Reference yield:

6-chloro-2-iodo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (403620-89-3) → 9-(3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-N6-methyl-2-phenylethynyladenine (879398-51-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / 4-(dimethylamino)pyridine / ethanol / Heating

2: 91 percent / triethylamine; CuI / (PPh₃)2PdCl₂ / dimethylformamide / 3 h / 20 °C

3: 72 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

4: 24.4 percent / trimethylsilyl trifluoromethanesulfonate; N,O-bis(trimethylsilyl)acetamide / acetonitrile / 10 h / Heating

5: 91 percent / ammonia / methanol / 2 h / 20 °C

With dmap; copper(l) iodide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; ammonia; triethylamine; trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2: Sonogashira coupling;

DOI:10.1016/j.bmc.2005.09.062

Reference yield:

3-azido-3-deoxy-1,2-di-O-acetyl-α-D-ribofuronamide → 9-(3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-N6-methyl-2-phenylethynyladenine (879398-51-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 24.4 percent / trimethylsilyl trifluoromethanesulfonate; N,O-bis(trimethylsilyl)acetamide / acetonitrile / 10 h / Heating

2: 91 percent / ammonia / methanol / 2 h / 20 °C

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; ammonia; In methanol; acetonitrile;

DOI:10.1016/j.bmc.2005.09.062

upstream raw materials:

N⁶-methyl-2-(phenylethynyl)adenine

2-iodo-N⁶-methyl-9-(tetrahydropyran-2-yl)adenine

N⁶-methyl-2-phenylethynyl-9-(tetrahydropyran-2-yl)adenine

6-chloro-2-iodo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

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