5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N⁶-isobutyryladenosine

Base Information

• Chemical Name: 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N⁶-isobutyryladenosine
• CAS No.: 853748-66-0
• Molecular Formula: C₃₉H₄₁F₃N₆O₈
• Molecular Weight: 778.785

Synonyms:5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N⁶-isobutyryladenosine

Chemical Property of 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N⁶-isobutyryladenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N⁶-isobutyryladenosine

There total 10 articles about 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N⁶-isobutyryladenosine 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: 71.0%

2'-O-(2-(trifluoroacetamido)ethyl)-N6-isobutyryladenosine (853748-65-9) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N6-isobutyryladenosine (853748-66-0)

Guidance literature:

With pyridine; at 20 ℃; for 24h;

DOI:10.1021/jo050061l

Reference yield:

methyl 2-(((2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl)oxy)acetate (304442-35-1) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N6-isobutyryladenosine (853748-66-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 93 percent / imidazole / dimethylformamide / 16 h

2.1: 94 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

3.1: trimethylsilyl chloride; pyridine / 1 h

3.2: 90 percent / pyridine / 5 h

4.1: 82 percent / Et₃N / CH₂Cl₂ / 1 h

5.1: 97 percent / NaN₃ / dimethylformamide / 3 h / 50 °C

6.1: H₂ / Pd/C / methanol / 1.5 h

7.1: 0.44 g / Et₃N / methanol / 4 h

8.1: 86 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

9.1: 71 percent / pyridine / 24 h / 20 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; chloro-trimethyl-silane; sodium azide; tetrabutyl ammonium fluoride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo050061l

Reference yield:

2-(((2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-3-yl)oxy)ethanol (853748-60-4) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(trifluoroacetamido)ethyl)-N6-isobutyryladenosine (853748-66-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: trimethylsilyl chloride; pyridine / 1 h

1.2: 90 percent / pyridine / 5 h

2.1: 82 percent / Et₃N / CH₂Cl₂ / 1 h

3.1: 97 percent / NaN₃ / dimethylformamide / 3 h / 50 °C

4.1: H₂ / Pd/C / methanol / 1.5 h

5.1: 0.44 g / Et₃N / methanol / 4 h

6.1: 86 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

7.1: 71 percent / pyridine / 24 h / 20 °C

With pyridine; chloro-trimethyl-silane; sodium azide; tetrabutyl ammonium fluoride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo050061l

upstream raw materials:

2'-O-(2-(trifluoroacetamido)ethyl)-N⁶-isobutyryladenosine

4,4'-dimethoxytrityl chloride

methyl 2-(((2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl)oxy)acetate

2-(((2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-3-yl)oxy)ethanol

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-(triphenylmethylthio)ethyl)-N⁶-isobutyryladenosine

3',5'-bis-O-(tert-butyldimethylsilyl)-2'-O-(2-(triphenylmethylthio)ethyl)-N⁶-isobutyryladenosine

2'-O-(2-(triphenylmethylthio)ethyl)-N⁶-isobutyryladenosine

Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-isobutyrylamino-purin-9-yl)-4-[2-(2,2,2-trifluoro-acetylamino)-ethoxy]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

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