(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(8-(4-nitrophenyl)-6-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(8-(4-nitrophenyl)-6-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate
• CAS No.: 1616623-57-4
• Molecular Formula: C₃₂H₄₀N₆O₁₃
• Molecular Weight: 716.702
• Mol file: 1616623-57-4.mol

Synonyms:(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(8-(4-nitrophenyl)-6-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

Chemical Property of (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(8-(4-nitrophenyl)-6-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)-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-(8-(4-nitrophenyl)-6-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

There total 5 articles about (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(8-(4-nitrophenyl)-6-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)-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: 68.0%

(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-bromo-8-(4-nitrophenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (1604818-48-5) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(8-(4-nitrophenyl)-6-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (1616623-57-4)

Guidance literature:

With triethylamine; at 80 ℃; for 8h;

DOI:10.1016/j.tet.2014.05.050

Reference yield:

p-nitrobenzene iodide (636-98-6) → (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(8-(4-nitrophenyl)-6-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (1616623-57-4)

Guidance literature:

Multi-step reaction with 4 steps

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

2: dmap; pyridine / 24 h / 20 °C

3: isopentyl nitrite; Bromoform / Bromoform / 3.5 h / 20 °C

4: triethylamine / 8 h / 80 °C

With pyridine; dmap; copper(l) iodide; Bromoform; palladium diacetate; caesium carbonate; triethylamine; isopentyl nitrite; In Bromoform; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2014.05.050

Reference yield:

(2R,3R,4S,5R)-2-(6-amino-8-(4-nitrophenyl)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (1037298-61-5) → (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(8-(4-nitrophenyl)-6-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (1616623-57-4)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; pyridine / 24 h / 20 °C

2: isopentyl nitrite; Bromoform / Bromoform / 3.5 h / 20 °C

3: triethylamine / 8 h / 80 °C

With pyridine; dmap; Bromoform; triethylamine; isopentyl nitrite; In Bromoform;

DOI:10.1016/j.tet.2014.05.050

upstream raw materials:

p-nitrobenzene iodide

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

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

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