4-Oxo-pentanoic acid (2R,3R,4R,5R)-4-[(2-chloro-phenoxy)-hydroxy-phosphoryloxy]-5-[6-(4-methoxy-benzoylamino)-purin-9-yl]-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: 4-Oxo-pentanoic acid (2R,3R,4R,5R)-4-[(2-chloro-phenoxy)-hydroxy-phosphoryloxy]-5-[6-(4-methoxy-benzoylamino)-purin-9-yl]-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 76998-93-1
• Molecular Formula: C₃₅H₃₉ClN₅O₁₃P
• Molecular Weight: 804.147

Synonyms:4-Oxo-pentanoic acid (2R,3R,4R,5R)-4-[(2-chloro-phenoxy)-hydroxy-phosphoryloxy]-5-[6-(4-methoxy-benzoylamino)-purin-9-yl]-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-ylmethyl ester

Chemical Property of 4-Oxo-pentanoic acid (2R,3R,4R,5R)-4-[(2-chloro-phenoxy)-hydroxy-phosphoryloxy]-5-[6-(4-methoxy-benzoylamino)-purin-9-yl]-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-ylmethyl ester

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Technology Process of 4-Oxo-pentanoic acid (2R,3R,4R,5R)-4-[(2-chloro-phenoxy)-hydroxy-phosphoryloxy]-5-[6-(4-methoxy-benzoylamino)-purin-9-yl]-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-ylmethyl ester

There total 5 articles about 4-Oxo-pentanoic acid (2R,3R,4R,5R)-4-[(2-chloro-phenoxy)-hydroxy-phosphoryloxy]-5-[6-(4-methoxy-benzoylamino)-purin-9-yl]-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-ylmethyl 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:

5'-O-levulinyl-3'-O-(4-methoxytetrahydropyran-4-yl)-6-N-p-anisoyladenosine 2'-O-(2-chlorophenyl 2,2,2-trichloroethyl phosphate) (76991-45-2) → 4-Oxo-pentanoic acid (2R,3R,4R,5R)-4-[(2-chloro-phenoxy)-hydroxy-phosphoryloxy]-5-[6-(4-methoxy-benzoylamino)-purin-9-yl]-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-ylmethyl ester (76998-93-1)

Guidance literature:

With 2,4,6-tri(iso-propyl)benzenesulfonic acid; zinc; In pyridine; at 35 ℃; for 0.05h;

DOI:10.1021/jo00324a010

Reference yield:

3'-O-(4-methoxytetrahydropyran-4-yl)-6-N-p-anisoyladenosine (71874-01-6) → 4-Oxo-pentanoic acid (2R,3R,4R,5R)-4-[(2-chloro-phenoxy)-hydroxy-phosphoryloxy]-5-[6-(4-methoxy-benzoylamino)-purin-9-yl]-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-ylmethyl ester (76998-93-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 40 percent / 2-chloro-1-methylpyridinium iodide, 1,4-diazabicyclo<2.2.2>octane / acetonitrile; dioxane / 2 h

2: 86 percent / 1-methylimidazole / acetonitrile / 0.75 h / 0 °C

3: activ. zinc, 2,4,6-triisopropylbenzenesulfonic acid (TPSOH) / pyridine / 0.05 h / 35 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1-methyl-1H-imidazole; 2,4,6-tri(iso-propyl)benzenesulfonic acid; 2-chloro-1-methyl-pyridinium iodide; zinc; In 1,4-dioxane; pyridine; acetonitrile;

DOI:10.1021/jo00324a010

Reference yield:

2,2,2-trichloroethyl 2-chlorophenyl phosphorochloridate (59819-52-2) → 4-Oxo-pentanoic acid (2R,3R,4R,5R)-4-[(2-chloro-phenoxy)-hydroxy-phosphoryloxy]-5-[6-(4-methoxy-benzoylamino)-purin-9-yl]-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-ylmethyl ester (76998-93-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / 1-methylimidazole / acetonitrile / 0.75 h / 0 °C

2: activ. zinc, 2,4,6-triisopropylbenzenesulfonic acid (TPSOH) / pyridine / 0.05 h / 35 °C

With 1-methyl-1H-imidazole; 2,4,6-tri(iso-propyl)benzenesulfonic acid; zinc; In pyridine; acetonitrile;

DOI:10.1021/jo00324a010

upstream raw materials:

5'-O-levulinyl-3'-O-(4-methoxytetrahydropyran-4-yl)-6-N-p-anisoyladenosine 2'-O-(2-chlorophenyl 2,2,2-trichloroethyl phosphate)

3'-O-(4-methoxytetrahydropyran-4-yl)-6-N-p-anisoyladenosine

2,2,2-trichloroethyl 2-chlorophenyl phosphorochloridate

5'-O-levulinyl-3'-O-(4-methoxytetrahydropyran-4-yl)-6-N-p-anisoyladenosine

Downstream raw materials:

C₆₇H₇₁Cl₅N₁₀O₂₃P₂

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