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

Base Information

Chemical Name:(2S,3S,4R,5R)-3-Azido-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide
CAS No.:786666-01-1
Molecular Formula:C₁₈H₁₇ClIN₉O₃
Molecular Weight:569.749
Hs Code.:

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

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

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

There total 13 articles about (2S,3S,4R,5R)-3-Azido-5-[2-chloro-6-(3-iodo-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-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-5-methylcarbamoyl-tetrahydro-furan-3-yl ester

: 786666-01-1
(2S,3S,4R,5R)-3-Azido-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 2h;
DOI:10.1016/j.bmcl.2004.07.042

Reference yield:

: 86945-40-6
3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranuronic acid

: 786666-01-1
(2S,3S,4R,5R)-3-Azido-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide

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: 210 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

Reference yield:

: 331729-05-6
3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranuronic acid methyl amide

: 786666-01-1
(2S,3S,4R,5R)-3-Azido-5-[2-chloro-6-(3-iodo-benzylamino)-purin-9-yl]-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide

Guidance literature:: Multi-step reaction with 4 steps

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

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

3.1: triethylamine / ethanol / Heating

4.1: 210 mg / ammonia / methanol / 24 h / 20 °C

With sulfuric acid; ammonia; triethylamine; In methanol; ethanol; 2.2: Vorbrueggen coupling;
DOI:10.1016/j.bmc.2004.11.044