(2S,3S,4R,5R)-3-Azido-5-[6-(5-chloro-2-methoxy-benzylamino)-purin-9-yl]-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide

Base Information

• Chemical Name: (2S,3S,4R,5R)-3-Azido-5-[6-(5-chloro-2-methoxy-benzylamino)-purin-9-yl]-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide
• CAS No.: 844665-73-2
• Molecular Formula: C₁₉H₂₀ClN₉O₄
• Molecular Weight: 473.879
• Mol file: 844665-73-2.mol

Synonyms:

Chemical Property of (2S,3S,4R,5R)-3-Azido-5-[6-(5-chloro-2-methoxy-benzylamino)-purin-9-yl]-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5R)-3-Azido-5-[6-(5-chloro-2-methoxy-benzylamino)-purin-9-yl]-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide

There total 7 articles about (2S,3S,4R,5R)-3-Azido-5-[6-(5-chloro-2-methoxy-benzylamino)-purin-9-yl]-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide 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:

Acetic acid (2R,3R,4S,5S)-4-azido-2-[6-(5-chloro-2-methoxy-benzylamino)-purin-9-yl]-5-methylcarbamoyl-tetrahydro-furan-3-yl ester → (2S,3S,4R,5R)-3-Azido-5-[6-(5-chloro-2-methoxy-benzylamino)-purin-9-yl]-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide (844665-73-2)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 24h;

DOI:10.1016/j.bmc.2004.11.044

Reference yield:

3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (23345-80-4) → (2S,3S,4R,5R)-3-Azido-5-[6-(5-chloro-2-methoxy-benzylamino)-purin-9-yl]-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide (844665-73-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 76.8 percent / NaIO₄; RuCl₃ hydrate / CHCl₃; acetonitrile; H₂O / 4.5 h / 20 °C

2.1: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 4-dimethylaminopyridine / 24 h / 20 °C

3.1: 1.2 g / tetrahydrofuran / 24 h / 55 °C

4.1: sulfuric acid; glacial acid / 18 h / 20 °C

5.2: trimethylsilyl triflate / 1,2-dichloro-ethane / Heating

6.1: triethylamine / ethanol / Heating

7.1: 251 mg / ammonia / methanol / 24 h / 20 °C

With dmap; ruthenium trichloride; sodium periodate; sulfuric acid; ammonia; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; ethanol; chloroform; water; acetonitrile; 5.2: Vorbrueggen coupling;

DOI:10.1016/j.bmc.2004.11.044

Reference yield:

3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranuronic acid (86945-40-6) → (2S,3S,4R,5R)-3-Azido-5-[6-(5-chloro-2-methoxy-benzylamino)-purin-9-yl]-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide (844665-73-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 4-dimethylaminopyridine / 24 h / 20 °C

2.1: 1.2 g / tetrahydrofuran / 24 h / 55 °C

3.1: sulfuric acid; glacial acid / 18 h / 20 °C

4.2: trimethylsilyl triflate / 1,2-dichloro-ethane / Heating

5.1: triethylamine / ethanol / Heating

6.1: 251 mg / ammonia / methanol / 24 h / 20 °C

With dmap; sulfuric acid; ammonia; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; ethanol; 4.2: Vorbrueggen coupling;

DOI:10.1016/j.bmc.2004.11.044

upstream raw materials:

3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranuronic acid

1,2-O-isopropylidene-3-azido-3-deoxy-α-D-ribofuranuronic acid methyl ester

3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranuronic acid methyl amide