3’-Deoxy-3’-fluoro-5’-O-(4,4’-dimethoxytrityl)thymidine

Base Information

• Chemical Name: 3’-Deoxy-3’-fluoro-5’-O-(4,4’-dimethoxytrityl)thymidine
• CAS No.: 290371-78-7
• Molecular Formula: C₃₁H₃₁FN₂O₆
• Molecular Weight: 546.595
• Mol file: 290371-78-7.mol

Synonyms:3’-Deoxy-3’-fluoro-5’-O-(4,4’-dimethoxytrityl)thymidine;5'-O-[Bis(4-Methoxyphenyl)phenylMethyl]-3'-deoxy-3'-fluorothyMidine

Chemical Property of 3’-Deoxy-3’-fluoro-5’-O-(4,4’-dimethoxytrityl)thymidine

Chemical Property:

• PSA: 92.04000
• LogP: 4.90880
• Solubility.: Dichloromethane,

Purity/Quality:

97% ^*data from raw suppliers

3’-Deoxy-3’-fluoro-5’-O-(4,4’-dimethoxytrityl)thymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3’-Deoxy-3’-fluoro-5’-O-(4,4’-dimethoxytrityl)thymidine (cas# 290371-78-7) is a compound useful in organic synthesis.

Technology Process of 3’-Deoxy-3’-fluoro-5’-O-(4,4’-dimethoxytrityl)thymidine

There total 4 articles about 3’-Deoxy-3’-fluoro-5’-O-(4,4’-dimethoxytrityl)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: 40.0%

1-((2R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)- dione (40615-39-2,104766-16-7,131607-26-6,131607-27-7,112501-53-8) → 5'-O-(4,4'-dimethoxytrityl)-3'-deoxy-3'-fluorothymidine (290371-78-7)

Guidance literature:

With pyridine; diethylamino-sulfur trifluoride; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jm201482p

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-2,3'-anhydrothymidine (191474-13-2) → 5'-O-(4,4'-dimethoxytrityl)-3'-deoxy-3'-fluorothymidine (290371-78-7)

Guidance literature:

With potassium fluoride; potassium carbonate; [2.2.2]cryptande; In dimethyl sulfoxide; at 175 ℃; for 1h;

DOI:10.1002/1099-1344(20001030)43:12<1211::AID-JLCR408>3.0.CO;2-#

Reference yield:

[5'-O-(4,4'-dimethoxytrityl)-O(2),O(3')-anhydro-1-(2-deoxy-β-D-threo-pentofuranosyl)]thymine → 5'-O-(4,4'-dimethoxytrityl)-3'-deoxy-3'-fluorothymidine (290371-78-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / ethanol / 1.5 h / 80 °C

2: pyridine; diethylamino-sulfur trifluoride / dichloromethane / 0 - 20 °C / Inert atmosphere

With pyridine; diethylamino-sulfur trifluoride; sodium hydroxide; In ethanol; dichloromethane;

DOI:10.1021/jm201482p

upstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-2,3'-anhydrothymidine

1-((2R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)- dione

5'-O-(4-4'-dimethoxytrityl)thymidine