4-Oxo-pentanoic acid 11-((2R,3S,4R,5R)-4-hydroxy-2-hydroxymethyl-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-3-yloxy)-undecyl ester

Base Information

• Chemical Name: 4-Oxo-pentanoic acid 11-((2R,3S,4R,5R)-4-hydroxy-2-hydroxymethyl-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-3-yloxy)-undecyl ester
• CAS No.: 191853-54-0
• Molecular Formula: C₃₅H₄₈N₆O₁₁
• Molecular Weight: 728.8

Synonyms:

Chemical Property of 4-Oxo-pentanoic acid 11-((2R,3S,4R,5R)-4-hydroxy-2-hydroxymethyl-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-3-yloxy)-undecyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Oxo-pentanoic acid 11-((2R,3S,4R,5R)-4-hydroxy-2-hydroxymethyl-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-3-yloxy)-undecyl ester

There total 8 articles about 4-Oxo-pentanoic acid 11-((2R,3S,4R,5R)-4-hydroxy-2-hydroxymethyl-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-3-yloxy)-undecyl 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:

1-Bromo-11-hydroxyundecane (1611-56-9) → 4-Oxo-pentanoic acid 11-((2R,3S,4R,5R)-4-hydroxy-2-hydroxymethyl-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-3-yloxy)-undecyl ester (191853-54-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 68 percent / 1H-imidazole / tetrahydrofuran

2: 88 percent / 1.) NaH; 2.) NaI / acetonitrile / 1.) room temp., 20 min.; 2.) room temp. overnight

3: 94 percent / Bu₄NF*3H₂O / tetrahydrofuran / Ambient temperature

4: 86 percent / EDC*HCl, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

5: 86 percent / 80percent AcOH / H₂O / 0.5 h / 100 °C

6: (NH₂₄)SO₄ / dioxane / 3 h / Heating

7: CH₂Cl₂

8: 80percent AcOH / H₂O / 1 h

With 1H-imidazole; dmap; (NH₂₄)SO₄; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium iodide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile;

DOI:10.1002/hlca.19970800313

Reference yield:

levulinic acid (123-76-2) → 4-Oxo-pentanoic acid 11-((2R,3S,4R,5R)-4-hydroxy-2-hydroxymethyl-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-3-yloxy)-undecyl ester (191853-54-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / EDC*HCl, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

2: 86 percent / 80percent AcOH / H₂O / 0.5 h / 100 °C

3: (NH₂₄)SO₄ / dioxane / 3 h / Heating

4: CH₂Cl₂

5: 80percent AcOH / H₂O / 1 h

With dmap; (NH₂₄)SO₄; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; dichloromethane; water;

DOI:10.1002/hlca.19970800313

Reference yield:

(11-bromoundecyloxy)dimethyl(1,1,2-trimethylpropyl)silane (191853-33-5) → 4-Oxo-pentanoic acid 11-((2R,3S,4R,5R)-4-hydroxy-2-hydroxymethyl-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-3-yloxy)-undecyl ester (191853-54-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / 1.) NaH; 2.) NaI / acetonitrile / 1.) room temp., 20 min.; 2.) room temp. overnight

2: 94 percent / Bu₄NF*3H₂O / tetrahydrofuran / Ambient temperature

3: 86 percent / EDC*HCl, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

4: 86 percent / 80percent AcOH / H₂O / 0.5 h / 100 °C

5: (NH₂₄)SO₄ / dioxane / 3 h / Heating

6: CH₂Cl₂

7: 80percent AcOH / H₂O / 1 h

With dmap; (NH₂₄)SO₄; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium iodide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile;

DOI:10.1002/hlca.19970800313

upstream raw materials:

1-Bromo-11-hydroxyundecane

levulinic acid

(11-bromoundecyloxy)dimethyl(1,1,2-trimethylpropyl)silane

4-Oxo-pentanoic acid 11-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-undecyl ester

Downstream raw materials:

4-Oxo-pentanoic acid 11-((2R,3S,4R,5R)-4-hydroxy-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-3-yloxy)-undecyl ester

4-Oxo-pentanoic acid 11-{(2R,3R,4R,5R)-2-hydroxymethyl-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-4-[2-(4-nitro-phenyl)-ethoxycarbonyloxy]-tetrahydro-furan-3-yloxy}-undecyl ester

4-Oxo-pentanoic acid 11-{(2R,3R,4R,5R)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-4-[2-(4-nitro-phenyl)-ethoxycarbonyloxy]-tetrahydro-furan-3-yloxy}-undecyl ester

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