(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-amino-8-(4-nitrophenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-amino-8-(4-nitrophenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate
• CAS No.: 1604818-47-4
• Molecular Formula: C₂₂H₂₂N₆O₉
• Molecular Weight: 514.451
• Mol file: 1604818-47-4.mol

Synonyms:(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-amino-8-(4-nitrophenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

Chemical Property of (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-amino-8-(4-nitrophenyl)-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-amino-8-(4-nitrophenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

There total 2 articles about (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-amino-8-(4-nitrophenyl)-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: 51.0%

(2R,3R,4S,5R)-2-(6-amino-8-(4-nitrophenyl)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (1037298-61-5) + acetic anhydride (108-24-7) → (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-amino-8-(4-nitrophenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (1604818-47-4)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 24h;

DOI:10.1002/ejoc.201301897

Reference yield:

adenosine (58-61-7) → (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-amino-8-(4-nitrophenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (1604818-47-4)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium diacetate; copper(l) iodide; piperidine / N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere

2: dmap; pyridine / 24 h / 20 °C

With piperidine; pyridine; dmap; copper(l) iodide; palladium diacetate; In N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201301897

Reference yield: 55.0%

(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-amino-8-(4-nitrophenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (1604818-47-4) → (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-bromo-8-(4-nitrophenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (1604818-48-5)

Guidance literature:

With Bromoform; isopentyl nitrite; at 20 ℃; for 3.5h;

DOI:10.1002/ejoc.201301897

upstream raw materials:

adenosine

(2R,3R,4S,5R)-2-(6-amino-8-(4-nitrophenyl)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

acetic anhydride

Downstream raw materials:

C₃₄H₃₂N₈O₉

C₃₆H₃₇N₉O₉

(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-bromo-8-(4-nitrophenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(8-(4-nitrophenyl)-6-(1,4,7,10,13-pentaoxa-16-azacyclooctadecan-16-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate