5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N⁶-benzoyl-2-(3-phenylpropyl)adenosine

Base Information

• Chemical Name: 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N⁶-benzoyl-2-(3-phenylpropyl)adenosine
• CAS No.: 504406-65-9
• Molecular Formula: C₅₃H₅₉N₅O₇Si
• Molecular Weight: 906.166

Synonyms:5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N⁶-benzoyl-2-(3-phenylpropyl)adenosine

Chemical Property of 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N⁶-benzoyl-2-(3-phenylpropyl)adenosine

Chemical Property:

Purity/Quality:

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Technology Process of 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N⁶-benzoyl-2-(3-phenylpropyl)adenosine

There total 6 articles about 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N⁶-benzoyl-2-(3-phenylpropyl)adenosine 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: 42.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 5'-O-(4,4'-dimethoxytrityl)-N6-benzoyl-2-(3-phenylpropyl)adenosine (504406-63-7) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N6-benzoyl-2-(3-phenylpropyl)adenosine (504406-65-9) + 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N6-benzoyl-2-(3-phenylpropyl)adenosine

Guidance literature:

With pyridine; silver nitrate; In tetrahydrofuran;

DOI:10.1021/ja021267w

Reference yield:

allylbenzene (300-57-2,57807-91-7) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N6-benzoyl-2-(3-phenylpropyl)adenosine (504406-65-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 53 percent / Pd(OAc)2; P(o-tol)3; Et₃N / acetonitrile / 80 °C

2.1: 85 percent / H₂ / 10 percent Pd/C / ethanol / 20 °C / atmospheric pressure

3.1: TMSCl; pyridine / 2 h / 20 °C

3.2: pyridine / 2.08 h / 0 - 20 °C

3.3: 68 percent / aq. NH₃ / pyridine / 0.25 h / 20 °C

4.1: 85 percent / pyridine

5.1: 42 percent / AgNO₃; pyrirdine / tetrahydrofuran

With pyridine; palladium diacetate; chloro-trimethyl-silane; hydrogen; silver nitrate; triethylamine; tris-(o-tolyl)phosphine; 10 percent Pd/C; In tetrahydrofuran; ethanol; acetonitrile; 1.1: Heck coupling;

DOI:10.1021/ja021267w

Reference yield:

2-iodoadenosine (35109-88-7) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N6-benzoyl-2-(3-phenylpropyl)adenosine (504406-65-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 53 percent / Pd(OAc)2; P(o-tol)3; Et₃N / acetonitrile / 80 °C

2.1: 85 percent / H₂ / 10 percent Pd/C / ethanol / 20 °C / atmospheric pressure

3.1: TMSCl; pyridine / 2 h / 20 °C

3.2: pyridine / 2.08 h / 0 - 20 °C

3.3: 68 percent / aq. NH₃ / pyridine / 0.25 h / 20 °C

4.1: 85 percent / pyridine

5.1: 42 percent / AgNO₃; pyrirdine / tetrahydrofuran

With pyridine; palladium diacetate; chloro-trimethyl-silane; hydrogen; silver nitrate; triethylamine; tris-(o-tolyl)phosphine; 10 percent Pd/C; In tetrahydrofuran; ethanol; acetonitrile; 1.1: Heck coupling;

DOI:10.1021/ja021267w

upstream raw materials:

tert-butyldimethylsilyl chloride

5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-2-(3-phenylpropyl)adenosine

allylbenzene

2-iodoadenosine

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