5,6-bis-TBDMS-5,6-dihydro-5-hydroxy-6-(2,5-dimethoxythiophenyl)thymidine

Base Information

• Chemical Name: 5,6-bis-TBDMS-5,6-dihydro-5-hydroxy-6-(2,5-dimethoxythiophenyl)thymidine
• CAS No.: 1374759-46-2
• Molecular Formula: C₃₀H₅₂N₂O₈SSi₂
• Molecular Weight: 656.988
• Mol file: 1374759-46-2.mol

Synonyms:5,6-bis-TBDMS-5,6-dihydro-5-hydroxy-6-(2,5-dimethoxythiophenyl)thymidine

Chemical Property of 5,6-bis-TBDMS-5,6-dihydro-5-hydroxy-6-(2,5-dimethoxythiophenyl)thymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,6-bis-TBDMS-5,6-dihydro-5-hydroxy-6-(2,5-dimethoxythiophenyl)thymidine

There total 2 articles about 5,6-bis-TBDMS-5,6-dihydro-5-hydroxy-6-(2,5-dimethoxythiophenyl)thymidine 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: 43.0%

2,5-dimethoxythiophenol (1483-27-8) + 5R,6S-bis-TBDMS-5,6-dihydro-5-hydroxy-6-benzoylthymidine (1374759-45-1) → 5,6-bis-TBDMS-5,6-dihydro-5-hydroxy-6-(2,5-dimethoxythiophenyl)thymidine (1374759-52-0) + 5,6-bis-TBDMS-5,6-dihydro-5-hydroxy-6-(2,5-dimethoxythiophenyl)thymidine (1374759-46-2)

Guidance literature:

With zinc(II) chloride; In diethyl ether; dichloromethane; at -80 ℃; for 2h; optical yield given as %de;

DOI:10.1021/ol301109z

Reference yield:

5R,6S-bis-TBDMS-thymidine glycol → 5,6-bis-TBDMS-5,6-dihydro-5-hydroxy-6-(2,5-dimethoxythiophenyl)thymidine (1374759-46-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; dmap / 12 h / 0 - 25 °C

2: zinc(II) chloride / diethyl ether; dichloromethane / 2 h / -80 °C

With pyridine; dmap; zinc(II) chloride; In diethyl ether; dichloromethane;

DOI:10.1021/ol301109z

Reference yield: 69.0%

5,6-bis-TBDMS-5,6-dihydro-5-hydroxy-6-(2,5-dimethoxythiophenyl)thymidine (1374759-46-2) + acetic anhydride (108-24-7) → C32H54N2O9SSi2 (1574501-93-1)

Guidance literature:

With dmap; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ja412562p

upstream raw materials:

2,5-dimethoxythiophenol

5R,6S-bis-TBDMS-5,6-dihydro-5-hydroxy-6-benzoylthymidine

Downstream raw materials:

C₁₈H₂₄N₂O₈S

5R,6S-5'-benzoyl-5,6-dihydro-6-(2,5-dimethoxythiophenyl)thymidine

5'-benzoyl-5,6-dihydro-5-hydroxy-thymidine

5'-DMT-5,6-dihydro-5S-acetyl-6S-(2,5-dimethoxythiophenyl)thymidine