N-[9-((2R,3R,4S,5R)-4-Benzyloxy-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide

Base Information

Chemical Name:N-[9-((2R,3R,4S,5R)-4-Benzyloxy-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide
CAS No.:184229-68-3
Molecular Formula:C₂₄H₂₃N₅O₅
Molecular Weight:461.477
Hs Code.:

Synonyms:N-[9-((2R,3R,4S,5R)-4-Benzyloxy-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide

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Chemical Property of N-[9-((2R,3R,4S,5R)-4-Benzyloxy-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide

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Technology Process of N-[9-((2R,3R,4S,5R)-4-Benzyloxy-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide

There total 7 articles about N-[9-((2R,3R,4S,5R)-4-Benzyloxy-3-hydroxy-5-hydroxymethyl-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:

: N-[9-((2R,3R,4S,5S)-4-Benzyloxy-5-formyl-3-hydroxy-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide

: 184229-68-3
N-[9-((2R,3R,4S,5R)-4-Benzyloxy-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide

Guidance literature:: With sodium tetrahydroborate; In methanol; for 0.5h; Yield given; Ambient temperature;
DOI:10.1021/ja961788h

Reference yield:

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

: 184229-68-3
N-[9-((2R,3R,4S,5R)-4-Benzyloxy-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide

Guidance literature:: Multi-step reaction with 5 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: NaIO₄ / tetrahydrofuran; H₂O / 2 h / Ambient temperature

5: NaBH₄ / methanol / 0.5 h / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; sodium periodate; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; pyridine; methanol; water; acetonitrile;
DOI:10.1021/ja961788h

Reference yield:

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

: 184229-68-3
N-[9-((2R,3R,4S,5R)-4-Benzyloxy-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide

Guidance literature:: Multi-step reaction with 6 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: NaIO₄ / tetrahydrofuran; H₂O / 2 h / Ambient temperature

6: NaBH₄ / methanol / 0.5 h / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; sodium periodate; trimethylsilyl trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; pyridine; methanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja961788h