5',3'-bis-O-tert-butyldimethylsilyl-5-[2-(4-N,N-dimethylaminophenyl)ethyl]-2'-deoxyuridine

Base Information

• Chemical Name: 5',3'-bis-O-tert-butyldimethylsilyl-5-[2-(4-N,N-dimethylaminophenyl)ethyl]-2'-deoxyuridine
• CAS No.: 289481-38-5
• Molecular Formula: C₃₁H₅₃N₃O₅Si₂
• Molecular Weight: 603.95

Synonyms:5',3'-bis-O-tert-butyldimethylsilyl-5-[2-(4-N,N-dimethylaminophenyl)ethyl]-2'-deoxyuridine

Chemical Property of 5',3'-bis-O-tert-butyldimethylsilyl-5-[2-(4-N,N-dimethylaminophenyl)ethyl]-2'-deoxyuridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of 5',3'-bis-O-tert-butyldimethylsilyl-5-[2-(4-N,N-dimethylaminophenyl)ethyl]-2'-deoxyuridine

There total 3 articles about 5',3'-bis-O-tert-butyldimethylsilyl-5-[2-(4-N,N-dimethylaminophenyl)ethyl]-2'-deoxyuridine 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: 80.2%

5',3'-bis-O-tert-butyldimethylsilyl-5-[2-(4-N,N-dimethylaminophenyl)ethynyl]-2'-deoxyuridine (289481-37-4) → 5',3'-bis-O-tert-butyldimethylsilyl-5-[2-(4-N,N-dimethylaminophenyl)ethyl]-2'-deoxyuridine (289481-38-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 48h; under 2585.74 Torr;

DOI:10.1080/15257770008033027

Reference yield:

4-ethynyl-N,N-dimethylaniline (17573-94-3,752235-18-0) → 5',3'-bis-O-tert-butyldimethylsilyl-5-[2-(4-N,N-dimethylaminophenyl)ethyl]-2'-deoxyuridine (289481-38-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TMSCl; hexamethyldisilazane / Heating

1.2: 61.2 percent / tetrakistriphenylphosphinepalladium⁽⁰⁾; CuI; Et₃N / tetrahydrofuran / 2 h / 60 °C

2.1: 80.2 percent / H₂ / Pd-C / methanol / 48 h / 20 °C / 2585.74 Torr

With chloro-trimethyl-silane; hydrogen; 1,1,1,3,3,3-hexamethyl-disilazane; palladium on activated charcoal; In methanol; 1.1: silylation / 1.2: cross-coupling / 2.1: Catalytic hydrogenation;

DOI:10.1080/15257770008033027

Reference yield:

2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)-5-iodouridine (148134-86-5) → 5',3'-bis-O-tert-butyldimethylsilyl-5-[2-(4-N,N-dimethylaminophenyl)ethyl]-2'-deoxyuridine (289481-38-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TMSCl; hexamethyldisilazane / Heating

1.2: 61.2 percent / tetrakistriphenylphosphinepalladium⁽⁰⁾; CuI; Et₃N / tetrahydrofuran / 2 h / 60 °C

2.1: 80.2 percent / H₂ / Pd-C / methanol / 48 h / 20 °C / 2585.74 Torr

With chloro-trimethyl-silane; hydrogen; 1,1,1,3,3,3-hexamethyl-disilazane; palladium on activated charcoal; In methanol; 1.1: silylation / 1.2: cross-coupling / 2.1: Catalytic hydrogenation;

DOI:10.1080/15257770008033027

upstream raw materials:

5',3'-bis-O-tert-butyldimethylsilyl-5-[2-(4-N,N-dimethylaminophenyl)ethynyl]-2'-deoxyuridine

2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)-5-iodouridine

4-ethynyl-N,N-dimethylaniline

Downstream raw materials:

5-[2-(4-N,N-dimethylaminophenyl)ethyl]-2'-deoxyuridine

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