(2S,3S,4R,5R) 3-azido-4-hydroxy-5-(6-[3-iodobenzylamino]-purin-9-yl)-tetrahydro-furan-2-carboxylic acid methylamide

Base Information

Chemical Name:(2S,3S,4R,5R) 3-azido-4-hydroxy-5-(6-[3-iodobenzylamino]-purin-9-yl)-tetrahydro-furan-2-carboxylic acid methylamide
CAS No.:786665-99-4
Molecular Formula:C₁₈H₁₈IN₉O₃
Molecular Weight:535.304
Hs Code.:

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

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

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

There total 16 articles about (2S,3S,4R,5R) 3-azido-4-hydroxy-5-(6-[3-iodobenzylamino]-purin-9-yl)-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: 89.0%

: 3718-88-5
3-iodobenzylamine hydrochloride

: 331729-03-4
(2S,3S,4R,5R)-3-azido-5-(6-chloro-purin-9-yl)-4-acetoxy-tetrahydro-furan-2-carboxylic acid methylamide

: 786665-99-4
(2S,3S,4R,5R) 3-azido-4-hydroxy-5-(6-[3-iodobenzylamino]-purin-9-yl)-tetrahydro-furan-2-carboxylic acid methylamide

Guidance literature:: 3-iodobenzylamine hydrochloride; (2S,3S,4R,5R)-3-azido-5-(6-chloro-purin-9-yl)-4-acetoxy-tetrahydro-furan-2-carboxylic acid methylamide; With triethylamine; In ethanol; at 50 ℃; for 18h;

With sodium methylate; In methanol; at 20 ℃; for 2h;
DOI:10.1021/jm050968b

Reference yield:

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

: 786665-99-4
(2S,3S,4R,5R) 3-azido-4-hydroxy-5-(6-[3-iodobenzylamino]-purin-9-yl)-tetrahydro-furan-2-carboxylic acid methylamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: oxalyl chloride / CH₂Cl₂; dimethylformamide / 16 h / 20 °C

2.1: 772 mg / tetrahydrofuran; CH₂Cl₂ / 3 h / 0 °C

3.1: 82 percent / AcOH; H₂SO₄ / 18 h / 20 °C

4.1: HMDS; ammonium sulfate / 16 h / Heating

4.2: 73 percent / TMSOTf / 1,2-dichloro-ethane / 2.33 h / 20 - 60 °C

5.1: Et₃N / ethanol / 18 h / 50 °C

5.2: 89 percent / NaOMe / methanol / 2 h / 20 °C

With ammonium sulfate; oxalyl dichloride; sulfuric acid; acetic acid; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm050968b

Reference yield:

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

: 786665-99-4
(2S,3S,4R,5R) 3-azido-4-hydroxy-5-(6-[3-iodobenzylamino]-purin-9-yl)-tetrahydro-furan-2-carboxylic acid methylamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 82 percent / AcOH; H₂SO₄ / 18 h / 20 °C

2.1: HMDS; ammonium sulfate / 16 h / Heating

2.2: 73 percent / TMSOTf / 1,2-dichloro-ethane / 2.33 h / 20 - 60 °C

3.1: Et₃N / ethanol / 18 h / 50 °C

3.2: 89 percent / NaOMe / methanol / 2 h / 20 °C

With ammonium sulfate; sulfuric acid; acetic acid; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In ethanol;
DOI:10.1021/jm050968b