Benzoic acid (2R,3R,5S)-5-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-(2-cyano-ethoxy)-phosphanyloxymethyl]-2-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,5S)-5-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-(2-cyano-ethoxy)-phosphanyloxymethyl]-2-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester
• CAS No.: 138824-83-6
• Molecular Formula: C₃₇H₃₆N₁₁O₁₀P
• Molecular Weight: 825.734
• Mol file: 138824-83-6.mol

Synonyms:

Chemical Property of Benzoic acid (2R,3R,5S)-5-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-(2-cyano-ethoxy)-phosphanyloxymethyl]-2-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3R,5S)-5-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-(2-cyano-ethoxy)-phosphanyloxymethyl]-2-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester

There total 7 articles about Benzoic acid (2R,3R,5S)-5-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-(2-cyano-ethoxy)-phosphanyloxymethyl]-2-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl 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:

cordycepin (73-03-0) → Benzoic acid (2R,3R,5S)-5-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-(2-cyano-ethoxy)-phosphanyloxymethyl]-2-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester (138824-83-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / pyridine / 2.5 h / 0 °C

2: 91 percent / 1.5 M aq. NaOH / methanol; tetrahydrofuran / 0.5 h / 0 °C

3: 84 percent / diisopropylethylamine / (dimethylamino)pyridine / pyridine / 4 h / Ambient temperature

4: 99 percent / triethylamine / (dimethylamino)pyridine / acetonitrile / 1.5 h / Ambient temperature

5: 99 percent / benzenesulfonic acid / CH₂Cl₂; methanol / 0.25 h / 0 °C

6: tetrazole / acetonitrile / 0.5 h / Ambient temperature

With pyridine; 1H-tetrazole; sodium hydroxide; triethylamine; N-ethyl-N,N-diisopropylamine; benzenesulfonic acid; dmap; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetonitrile;

DOI:10.1021/jo00052a053

Reference yield:

N-(9-((2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide (76902-49-3) → Benzoic acid (2R,3R,5S)-5-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-(2-cyano-ethoxy)-phosphanyloxymethyl]-2-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester (138824-83-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / diisopropylethylamine / (dimethylamino)pyridine / pyridine / 4 h / Ambient temperature

2: 99 percent / triethylamine / (dimethylamino)pyridine / acetonitrile / 1.5 h / Ambient temperature

3: 99 percent / benzenesulfonic acid / CH₂Cl₂; methanol / 0.25 h / 0 °C

4: tetrazole / acetonitrile / 0.5 h / Ambient temperature

With 1H-tetrazole; triethylamine; N-ethyl-N,N-diisopropylamine; benzenesulfonic acid; dmap; In pyridine; methanol; dichloromethane; acetonitrile;

DOI:10.1021/jo00052a053

Reference yield:

N-(9-((2R,3R,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-hydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide (84138-86-3) → Benzoic acid (2R,3R,5S)-5-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-(2-cyano-ethoxy)-phosphanyloxymethyl]-2-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester (138824-83-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / triethylamine / (dimethylamino)pyridine / acetonitrile / 1.5 h / Ambient temperature

2: 99 percent / benzenesulfonic acid / CH₂Cl₂; methanol / 0.25 h / 0 °C

3: tetrazole / acetonitrile / 0.5 h / Ambient temperature

With 1H-tetrazole; triethylamine; benzenesulfonic acid; dmap; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/jo00052a053

upstream raw materials:

N⁶,O^2'-dibenzoyl-3'-deoxyadenosine

Diisopropyl-phosphoramidous acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-cyano-ethyl ester

cordycepin

3'-azido-2',3'-deoxythymidine