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

Base Information

• Chemical Name: 1-{N₃-[5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-thymidylyl]}-4-{N₃-[5'-O-(levulinoyl)-3'-O-(allyloxycarbonyl)-thymidylyl]}butane
• CAS No.: 1393343-45-7
• Molecular Formula: C₆₀H₇₆N₄O₁₆Si
• Molecular Weight: 1137.37

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

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

There total 2 articles about 1-{N₃-[5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-thymidylyl]}-4-{N₃-[5'-O-(levulinoyl)-3'-O-(allyloxycarbonyl)-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: 68.0%

5'-O-levulinoyl-3'-O-allyloxycarbonyl-thymidine (1393343-44-6) + N3-(4-iodobutyl)-5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-thymidine (749254-18-0) → 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)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 24h;

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)-3'-O-(allyloxycarbonyl)-thymidylyl]}butane (1393343-45-7)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine; dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.tet.2012.07.043

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

upstream raw materials:

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

N₃-(4-iodobutyl)-5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-thymidine

Downstream raw materials:

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

C₆₅H₈₉N₆O₁₅PSi

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