5-Nitro-2-(4-oxo-pentanoyloxymethyl)-benzoic acid (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: 5-Nitro-2-(4-oxo-pentanoyloxymethyl)-benzoic acid (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 224052-17-9
• Molecular Formula: C₂₇H₃₁N₃O₁₃
• Molecular Weight: 605.555

Synonyms:

Chemical Property of 5-Nitro-2-(4-oxo-pentanoyloxymethyl)-benzoic acid (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of 5-Nitro-2-(4-oxo-pentanoyloxymethyl)-benzoic acid (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-ylmethyl ester

There total 4 articles about 5-Nitro-2-(4-oxo-pentanoyloxymethyl)-benzoic acid (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-4-(tetrahydro-pyran-2-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:

2-benzofuran-1(3H)-one (87-41-2) → 5-Nitro-2-(4-oxo-pentanoyloxymethyl)-benzoic acid (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-ylmethyl ester (224052-17-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / KOH / methanol; H₂O / 2 h / Heating

2: 59 percent / 1-methylimidazole / dioxane / 1 h

3: 62 percent / H₂SO₄, HNO₃ / 1 h / 0 °C

4: 2,4,6-triisopropylbenzenesulfonyl chloride / pyridine / Ambient temperature

With 1-methyl-1H-imidazole; potassium hydroxide; 2,4,6-triisopropylphenylsulfonyl chloride; sulfuric acid; nitric acid; In 1,4-dioxane; pyridine; methanol; water;

DOI:10.1016/S0040-4039(97)01617-1

Reference yield:

2-(hydroxymethyl)benzoic acid (612-20-4) → 5-Nitro-2-(4-oxo-pentanoyloxymethyl)-benzoic acid (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-ylmethyl ester (224052-17-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 59 percent / 1-methylimidazole / dioxane / 1 h

2: 62 percent / H₂SO₄, HNO₃ / 1 h / 0 °C

3: 2,4,6-triisopropylbenzenesulfonyl chloride / pyridine / Ambient temperature

With 1-methyl-1H-imidazole; 2,4,6-triisopropylphenylsulfonyl chloride; sulfuric acid; nitric acid; In 1,4-dioxane; pyridine;

DOI:10.1016/S0040-4039(97)01617-1

Reference yield:

2-(4-Oxo-pentanoyloxymethyl)-benzoic acid (189256-18-6) → 5-Nitro-2-(4-oxo-pentanoyloxymethyl)-benzoic acid (2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-ylmethyl ester (224052-17-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / H₂SO₄, HNO₃ / 1 h / 0 °C

2: 2,4,6-triisopropylbenzenesulfonyl chloride / pyridine / Ambient temperature

With 2,4,6-triisopropylphenylsulfonyl chloride; sulfuric acid; nitric acid; In pyridine;

DOI:10.1016/S0040-4039(97)01617-1

upstream raw materials:

5-Nitro-2-(4-oxo-pentanoyloxymethyl)-benzoic acid

O^2'-tetrahydropyran-2-yl-uridine

2-benzofuran-1(3H)-one

2-(hydroxymethyl)benzoic acid

Downstream raw materials:

5-Nitro-2-(4-oxo-pentanoyloxymethyl)-benzoic acid (2R,3R,4R,5R)-3-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-ylmethyl ester

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