2,4,6-Triisopropyl-benzenesulfonic acid 1-((2R,3R,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl ester

Base Information

• Chemical Name: 2,4,6-Triisopropyl-benzenesulfonic acid 1-((2R,3R,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl ester
• CAS No.: 136055-16-8
• Molecular Formula: C₃₃H₅₈N₂O₈SSi₃
• Molecular Weight: 727.155
• Mol file: 136055-16-8.mol

Synonyms:2,4,6-Triisopropyl-benzenesulfonic acid 1-((2R,3R,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl ester

Chemical Property of 2,4,6-Triisopropyl-benzenesulfonic acid 1-((2R,3R,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4,6-Triisopropyl-benzenesulfonic acid 1-((2R,3R,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl ester

There total 2 articles about 2,4,6-Triisopropyl-benzenesulfonic acid 1-((2R,3R,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-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: 54.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + 2',3',5,-tris-O-(trimethylsilyl)uridine (10457-16-6) → 2,4,6-Triisopropyl-benzenesulfonic acid 1-((2R,3R,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl ester (136055-16-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran;

DOI:10.1016/0040-4039(91)80679-Z

Reference yield:

uridine (58-96-8) → 2,4,6-Triisopropyl-benzenesulfonic acid 1-((2R,3R,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl ester (136055-16-8)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 2 h / Heating

2: Bu₄NBr; aq. Na₂CO₃ / CH₂Cl₂ / 16 h / 20 °C

With tetrabutylammomium bromide; sodium carbonate; In dichloromethane; acetonitrile; 1: silylation / 2: Substitution;

DOI:10.1021/jo991432z

Reference yield:

2,4,6-Triisopropyl-benzenesulfonic acid 1-((2R,3R,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl ester (136055-16-8) → 4-thiouridine (13957-31-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 54 percent / K₂CO₃ / aq. ethanol / 3 h / 25 °C

2: AcOH / tetrahydrofuran; H₂O

3: 95 percent / conc. NH₄OH / 0.5 h / 25 °C

With ammonium hydroxide; potassium carbonate; acetic acid; In tetrahydrofuran; ethanol; water;

DOI:10.1016/0040-4039(91)80679-Z

upstream raw materials:

2,4,6-triisopropylphenylsulfonyl chloride

2',3',5,-tris-O-(trimethylsilyl)uridine

uridine

Downstream raw materials:

4-S-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-4-thiouridine

5′-O-(4,4′-dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-4-(2-cyanoethylthio)uridine

4-thiouridine