5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N²-isobutyrylguanosine

Base Information

• Chemical Name: 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N²-isobutyrylguanosine
• CAS No.: 853748-78-4
• Molecular Formula: C₃₉H₄₁F₃N₆O₉
• Molecular Weight: 794.785

Synonyms:5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N²-isobutyrylguanosine

Chemical Property of 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N²-isobutyrylguanosine

Chemical Property:

Purity/Quality:

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Technology Process of 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N²-isobutyrylguanosine

There total 11 articles about 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N²-isobutyrylguanosine 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: 83.0%

2'-O-(2-(trifluoroacetamido)ethyl)-N2-isobutyrylguanosine (853748-77-3) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N2-isobutyrylguanosine (853748-78-4)

Guidance literature:

With pyridine; at 20 ℃; for 18h;

DOI:10.1021/jo050061l

Reference yield:

3',5'-bis(tert-butyldimethylsilyl)-2'-O-(2-azidoethyl)-N2-isobutyrylguanosine (853748-76-2) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N2-isobutyrylguanosine (853748-78-4)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Pd/C / ethanol / 12 h

2: Et₃N / tetrahydrofuran / 12 h

3: 0.190 g / TBAF / tetrahydrofuran / 6 h / 20 °C

4: 83 percent / pyridine / 18 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1021/jo050061l

Reference yield:

3',5',O6-tris(tert-butyldimethylsilyl)-2'-O-(2-benzyloxyethyl)guanosine (853748-73-9) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N2-isobutyrylguanosine (853748-78-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / pyridine / 0.75 h

2: 88 percent / H₂ / Pd/C / ethanol / 12 h

3: 98 percent / Et₃N / CH₂Cl₂ / 1 h

4: 70 percent / NaN₃; 18-crown-6 / dimethylformamide / 5 h / 60 °C

5: H₂ / Pd/C / ethanol / 12 h

6: Et₃N / tetrahydrofuran / 12 h

7: 0.190 g / TBAF / tetrahydrofuran / 6 h / 20 °C

8: 83 percent / pyridine / 18 h / 20 °C

With pyridine; sodium azide; 18-crown-6 ether; tetrabutyl ammonium fluoride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo050061l

upstream raw materials:

2'-O-(2-(trifluoroacetamido)ethyl)-N²-isobutyrylguanosine

4,4'-dimethoxytrityl chloride

3',5'-bis(tert-butyldimethylsilyl)-2'-O-(2-azidoethyl)-N²-isobutyrylguanosine

3',5',O⁶-tris(tert-butyldimethylsilyl)-2'-O-(2-benzyloxyethyl)guanosine

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