(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(4-methoxyphenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(4-methoxyphenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate
• CAS No.: 279670-58-5
• Molecular Formula: C₂₃H₂₄N₄O₈
• Molecular Weight: 484.466
• Mol file: 279670-58-5.mol

Synonyms:(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(4-methoxyphenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

Chemical Property of (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(4-methoxyphenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(4-methoxyphenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

There total 5 articles about (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(4-methoxyphenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 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: 84.0%

2',3',5'-O-triacetyl-6-chloroinosine (5987-73-5) + 4-methoxyphenylboronic acid (5720-07-0) → (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(4-methoxyphenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (279670-58-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In toluene; at 100 ℃; for 8h;

DOI:10.1021/jm991167+

Reference yield: 78.0%

9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-[(3-methylbutyl)sulfanyl]purine + 4-methoxyphenylboronic acid (5720-07-0) → (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(4-methoxyphenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (279670-58-5)

Guidance literature:

With 1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene hydrochloride; potassium carbonate; palladium diacetate; In toluene; at 90 ℃; for 8h;

DOI:10.1021/ol050063s

Reference yield:

2',3',5'-O-triacetyl-6-chloroinosine (5987-73-5) → (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(4-methoxyphenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (279670-58-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / DBU / acetonitrile / 20 °C

2: 78 percent / 1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene*HCl; K₂CO₃ / Pd(OAc)2 / toluene / 8 h / 90 °C

With 1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene hydrochloride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium diacetate; In toluene; acetonitrile; 2: Suzuki cross-coupling;

DOI:10.1021/ol050063s

upstream raw materials:

2',3',5'-O-triacetyl-6-chloroinosine

4-methoxyphenylboronic acid

inosine

2’,3’,5’-tri-O-acetylinosine