N-{9-[(2R,4S,5R)-4-Benzyloxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide

Base Information

Chemical Name:N-{9-[(2R,4S,5R)-4-Benzyloxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide
CAS No.:184229-65-0
Molecular Formula:C₂₅H₂₅N₅O₄
Molecular Weight:459.505
Hs Code.:

Synonyms:N-{9-[(2R,4S,5R)-4-Benzyloxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide

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Chemical Property of N-{9-[(2R,4S,5R)-4-Benzyloxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide

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Technology Process of N-{9-[(2R,4S,5R)-4-Benzyloxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide

There total 9 articles about N-{9-[(2R,4S,5R)-4-Benzyloxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide 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: 76.0%

: 184229-64-9
N-(9-{(2R,4S,5R)-4-Benzyloxy-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide

: 184229-65-0
N-{9-[(2R,4S,5R)-4-Benzyloxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 5h; Ambient temperature;
DOI:10.1021/ja961788h

Reference yield:

: 14686-89-6
(1,2:5,6)-di-O-isopropylidene-D-gulose

: 184229-65-0
N-{9-[(2R,4S,5R)-4-Benzyloxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide

Guidance literature:: Multi-step reaction with 8 steps

1: sodium hydride / dimethylformamide / 1 h / Ambient temperature

2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating

3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C

4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature

5: 97 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

6: 90 percent / tetrahydrofuran / 12 h / 65 °C

7: 80 percent / Bu₃SnH, azobisisobutyronitrile / toluene / 1.5 h / 75 °C

8: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature

With 1H-imidazole; sodium hydroxide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/ja961788h

Reference yield:

: 22331-21-1
1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose

: 184229-65-0
N-{9-[(2R,4S,5R)-4-Benzyloxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide

Guidance literature:: Multi-step reaction with 7 steps

1: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating

2: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C

3: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature

4: 97 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

5: 90 percent / tetrahydrofuran / 12 h / 65 °C

6: 80 percent / Bu₃SnH, azobisisobutyronitrile / toluene / 1.5 h / 75 °C

7: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature

With 1H-imidazole; sodium hydroxide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; pyridine; dichloromethane; toluene; acetonitrile;
DOI:10.1021/ja961788h