1-((2S,4R,5S)-4-Fluoro-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-((2S,4R,5S)-4-Fluoro-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
• CAS No.: 207128-21-0
• Molecular Formula: C₂₈H₂₅FN₂O₄
• Molecular Weight: 472.516
• Mol file: 207128-21-0.mol

Synonyms:1-((2S,4R,5S)-4-Fluoro-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Chemical Property of 1-((2S,4R,5S)-4-Fluoro-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-((2S,4R,5S)-4-Fluoro-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

There total 5 articles about 1-((2S,4R,5S)-4-Fluoro-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 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: 47.7%

1-((2S,4S,5S)-4-Hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione (207128-18-5) → 1-((2S,4R,5S)-4-Fluoro-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione (207128-21-0)

Guidance literature:

With 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jm9704210

Reference yield:

trityl chloride (76-83-5) → 1-((2S,4R,5S)-4-Fluoro-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione (207128-21-0)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 1 h / 100 °C

2: pyridine / Ambient temperature

3: 46.6 percent / NaOH / ethanol / 2 h / Heating

4: 47.7 percent / DAST / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; sodium hydroxide; 4,4'-diaminostilbene-2,2'-disulfonic acid; In ethanol; dichloromethane;

DOI:10.1021/jm9704210

Reference yield:

Methanesulfonic acid (2S,3R,5S)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester (207128-16-3) → 1-((2S,4R,5S)-4-Fluoro-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione (207128-21-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 46.6 percent / NaOH / ethanol / 2 h / Heating

2: 47.7 percent / DAST / CH₂Cl₂ / 1 h / Ambient temperature

With sodium hydroxide; 4,4'-diaminostilbene-2,2'-disulfonic acid; In ethanol; dichloromethane;

DOI:10.1021/jm9704210

upstream raw materials:

1-((2S,4S,5S)-4-Hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

trityl chloride

Methanesulfonic acid (2S,3R,5S)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester

5'-O-trityl-2'-deoxy-L-uridine

Downstream raw materials:

β-2',3'-dideoxy-3'-fluoro-L-uridine

β-L-2',3'-dideoxy-3'-fluorocytidine