Thymidine, 3'-O-(azidomethyl)-, 5'-benzoate

Base Information

• Chemical Name: Thymidine, 3'-O-(azidomethyl)-, 5'-benzoate
• CAS No.: 139433-18-4
• Molecular Formula: C18H19N5O6
• Molecular Weight: 401.379
• Mol file: 139433-18-4.mol

Synonyms:

Chemical Property of Thymidine, 3'-O-(azidomethyl)-, 5'-benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Thymidine, 3'-O-(azidomethyl)-, 5'-benzoate

There total 2 articles about Thymidine, 3'-O-(azidomethyl)-, 5'-benzoate 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: 82.5%

5'-O-benzoyl-3'-O-(methylthiomethyl)thymidine (139432-97-6) → 3'-O-(azidomethyl)-5'-O-benzoylthymidine (139433-18-4)

Guidance literature:

5'-O-benzoyl-3'-O-(methylthiomethyl)thymidine; With bromine; In acetonitrile; at 0 ℃; for 0.5h;

With lithium azide; In acetonitrile; at 0 - 60 ℃; for 2.16667h;

DOI:10.1021/jo400651k

Reference yield:

5'-benzoylthymidine (35898-29-4,65475-51-6) → 3'-O-(azidomethyl)-5'-O-benzoylthymidine (139433-18-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic anhydride / acetic acid / 72 h / 20 °C

2.1: bromine / acetonitrile / 0.5 h / 0 °C

2.2: 2.17 h / 0 - 60 °C

With bromine; acetic anhydride; In acetic acid; acetonitrile; 1.1: |Pummerer Sulfoxide Rearrangement;

DOI:10.1021/jo400651k

Reference yield: 94.6%

3'-O-(azidomethyl)-5'-O-benzoylthymidine (139433-18-4) → 3'-O-(azidomethyl)-2'-deoxythymidine (136041-38-8)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 12h;

DOI:10.1021/jo400651k

upstream raw materials:

5'-benzoylthymidine

5'-O-benzoyl-3'-O-(methylthiomethyl)thymidine

Downstream raw materials:

3'-O-(azidomethyl)-5'-O-(4,4'-dimethoxytrityl)thymidine

C₅₉H₆₃N₇O₁₁Si

C₄₃H₄₅N₇O₁₁

C₅₂H₆₂N₉O₁₂P