4-Oxo-pentanoic acid (2R,3S,5R)-2-(2-benzenesulfonyl-ethoxycarbonyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: 4-Oxo-pentanoic acid (2R,3S,5R)-2-(2-benzenesulfonyl-ethoxycarbonyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• CAS No.: 80667-95-4
• Molecular Formula: C₂₄H₂₈N₂O₁₁S
• Molecular Weight: 552.559
• Mol file: 80667-95-4.mol

Synonyms:4-Oxo-pentanoic acid (2R,3S,5R)-2-(2-benzenesulfonyl-ethoxycarbonyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Chemical Property of 4-Oxo-pentanoic acid (2R,3S,5R)-2-(2-benzenesulfonyl-ethoxycarbonyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Oxo-pentanoic acid (2R,3S,5R)-2-(2-benzenesulfonyl-ethoxycarbonyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

There total 1 articles about 4-Oxo-pentanoic acid (2R,3S,5R)-2-(2-benzenesulfonyl-ethoxycarbonyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-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: 80.0%

3'-O-levulinoylthymidine (78635-98-0) + 2-Phenylsulfonylethylchloroformate (PSEC) (74063-48-2) → 4-Oxo-pentanoic acid (2R,3S,5R)-2-(2-benzenesulfonyl-ethoxycarbonyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (80667-95-4)

Guidance literature:

In pyridine; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4039(01)81988-2

Reference yield: 96.7%

4-Oxo-pentanoic acid (2R,3S,5R)-2-(2-benzenesulfonyl-ethoxycarbonyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (80667-95-4) → Carbonic acid 2-benzenesulfonyl-ethyl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (80667-97-6)

Guidance literature:

With hydrazine; In pyridine; acetic acid; at 20 ℃;

DOI:10.1016/S0040-4039(01)81988-2

Reference yield:

4-Oxo-pentanoic acid (2R,3S,5R)-2-(2-benzenesulfonyl-ethoxycarbonyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (80667-95-4) → 3'-O-benzoylthymidine (17331-53-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 96.7 percent / N₂H₄ / pyridine; acetic acid / 20 °C

2: Benzoylation

3: 84.7 percent / Triethylamine / pyridine / 20 h / 20 °C

With triethylamine; hydrazine; In pyridine; acetic acid;

DOI:10.1016/S0040-4039(01)81988-2

upstream raw materials:

3'-O-levulinoylthymidine

2-Phenylsulfonylethylchloroformate (PSEC)

Downstream raw materials:

Carbonic acid 2-benzenesulfonyl-ethyl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

C₃₅H₃₈ClN₄O₁₆PS

C₄₅H₄₂ClN₄O₁₃P

C₅₄H₅₀ClN₄O₁₇PS