1-[3-fluoro-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydroselenophen-2-yl]-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[3-fluoro-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydroselenophen-2-yl]-1H-pyrimidine-2,4-dione
• CAS No.: 1187425-03-1
• Molecular Formula: C₃₃H₃₃FN₂O₅Se
• Molecular Weight: 635.594

Synonyms:1-[3-fluoro-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydroselenophen-2-yl]-1H-pyrimidine-2,4-dione

Chemical Property of 1-[3-fluoro-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydroselenophen-2-yl]-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

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Technology Process of 1-[3-fluoro-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydroselenophen-2-yl]-1H-pyrimidine-2,4-dione

There total 18 articles about 1-[3-fluoro-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydroselenophen-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: 23.0%

1-[3-hydroxy-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydroselenophen-2-yl]-1H-pyrimidine-2,4-dione (1187425-02-0) → 1-hydroxy-2-trityloxymethyl-1,2,3a,8a-tetrahydro-8-oxa-3-selena-3b,7-diazacyclopenta[a]inden-6-one (1146697-60-0) + 1-[3-fluoro-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydroselenophen-2-yl]-1H-pyrimidine-2,4-dione (1187425-03-1)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; at -78 - 0 ℃;

DOI:10.1021/jm900852b

Reference yield:

1-[3-hydroxy-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydroselenophen-2-yl]-1H-pyrimidine-2,4-dione (1187425-02-0) → 1-[3-fluoro-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydroselenophen-2-yl]-1H-pyrimidine-2,4-dione (1187425-03-1)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; at -78 - 0 ℃; for 2.5h; stereoselective reaction;

DOI:10.1016/j.ejmech.2014.06.031

Reference yield:

1-(2,2’-anhydro-4-seleno-β-D-ribofuranosyl)uracil (1620879-55-1) → 1-[3-fluoro-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydroselenophen-2-yl]-1H-pyrimidine-2,4-dione (1187425-03-1)

Guidance literature:

Multi-step reaction with 4 steps

1: dmap; pyridine / 15 h / 20 - 55 °C

2: pyridinium p-toluenesulfonate / dichloromethane / 20 h / 0 - 20 °C

3: sodium hydroxide / acetonitrile / 2 h / 20 °C

4: diethylamino-sulfur trifluoride / dichloromethane / 2.5 h / -78 - 0 °C

With pyridine; dmap; diethylamino-sulfur trifluoride; pyridinium p-toluenesulfonate; sodium hydroxide; In dichloromethane; acetonitrile;

DOI:10.1016/j.ejmech.2014.06.031

upstream raw materials:

1-[3-hydroxy-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydroselenophen-2-yl]-1H-pyrimidine-2,4-dione

1-[2,2’-anhydro-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-β-D-ribofuranosyl]uracil

1-(2,2’-anhydro-4-seleno-β-D-ribofuranosyl)uracil

1-hydroxy-2-trityloxymethyl-1,2,3a,8a-tetrahydro-8-oxa-3-selena-3b,7-diazacyclopenta[a]inden-6-one

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