1-{N₃-[5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-thymidylyl]}-4-{N₃-[5'-O-(levulinoyl)-thymidylyl]}butane

Base Information

• Chemical Name: 1-{N₃-[5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-thymidylyl]}-4-{N₃-[5'-O-(levulinoyl)-thymidylyl]}butane
• CAS No.: 1393343-46-8
• Molecular Formula: C₅₆H₇₂N₄O₁₄Si
• Molecular Weight: 1053.29

Synonyms:1-{N₃-[5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-thymidylyl]}-4-{N₃-[5'-O-(levulinoyl)-thymidylyl]}butane

Chemical Property of 1-{N₃-[5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-thymidylyl]}-4-{N₃-[5'-O-(levulinoyl)-thymidylyl]}butane

Chemical Property:

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Technology Process of 1-{N₃-[5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-thymidylyl]}-4-{N₃-[5'-O-(levulinoyl)-thymidylyl]}butane

There total 3 articles about 1-{N₃-[5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-thymidylyl]}-4-{N₃-[5'-O-(levulinoyl)-thymidylyl]}butane 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: 100.0%

1-{N3-[5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-thymidylyl]}-4-{N3-[5'-O-(levulinoyl)-3'-O-(allyloxycarbonyl)-thymidylyl]}butane (1393343-45-7) → 1-{N3-[5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-thymidylyl]}-4-{N3-[5'-O-(levulinoyl)-thymidylyl]}butane (1393343-46-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; N-butylamine; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 2.5h;

DOI:10.1016/j.tet.2012.07.043

Reference yield:

5'-O-levulinoyl-β-D-thymidine → 1-{N3-[5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-thymidylyl]}-4-{N3-[5'-O-(levulinoyl)-thymidylyl]}butane (1393343-46-8)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; dmap / tetrahydrofuran / 24 h / 20 °C

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 24 h / 20 °C

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; N-butylamine; triphenylphosphine / tetrahydrofuran / 2.5 h / 20 °C

With pyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-butylamine; triphenylphosphine; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.tet.2012.07.043

Reference yield:

5'-O-levulinoyl-3'-O-allyloxycarbonyl-thymidine (1393343-44-6) → 1-{N3-[5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-thymidylyl]}-4-{N3-[5'-O-(levulinoyl)-thymidylyl]}butane (1393343-46-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 24 h / 20 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; N-butylamine; triphenylphosphine / tetrahydrofuran / 2.5 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-butylamine; triphenylphosphine; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.tet.2012.07.043

upstream raw materials:

5'-O-levulinoyl-3'-O-allyloxycarbonyl-thymidine

1-{N₃-[5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-thymidylyl]}-4-{N₃-[5'-O-(levulinoyl)-3'-O-(allyloxycarbonyl)-thymidylyl]}butane

Downstream raw materials:

C₆₅H₈₉N₆O₁₅PSi

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