Benzoic acid 9-((2S,3S,4S,5S)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid 9-((2S,3S,4S,5S)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylmethyl ester
• CAS No.: 915022-17-2
• Molecular Formula: C₂₄H₂₄N₄O₉
• Molecular Weight: 512.476

Synonyms:Benzoic acid 9-((2S,3S,4S,5S)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylmethyl ester

Chemical Property of Benzoic acid 9-((2S,3S,4S,5S)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylmethyl ester

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Technology Process of Benzoic acid 9-((2S,3S,4S,5S)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylmethyl ester

There total 3 articles about Benzoic acid 9-((2S,3S,4S,5S)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylmethyl ester 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: 88.0%

6-chloro-9-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)purine (915022-08-1) + [(benzoyloxy)methyl]zinc iodide (14135-39-8) → Benzoic acid 9-((2S,3S,4S,5S)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylmethyl ester (915022-17-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.bmcl.2006.07.092

Reference yield:

6-chloropurine (87-42-3) → Benzoic acid 9-((2S,3S,4S,5S)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylmethyl ester (915022-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / SnCl₄ / acetonitrile / 10 h / 20 °C

2: 88 percent / Pd(PPh₃)4 / tetrahydrofuran / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tin(IV) chloride; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.bmcl.2006.07.092

Reference yield:

1,2,3,5-tetra-O-acetyl-β-L-ribofuranose (144490-03-9) → Benzoic acid 9-((2S,3S,4S,5S)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylmethyl ester (915022-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / SnCl₄ / acetonitrile / 10 h / 20 °C

2: 88 percent / Pd(PPh₃)4 / tetrahydrofuran / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tin(IV) chloride; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.bmcl.2006.07.092

upstream raw materials:

6-chloro-9-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)purine

[(benzoyloxy)methyl]zinc iodide

6-chloropurine

1,2,3,5-tetra-O-acetyl-β-L-ribofuranose

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