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

Base Information

• Chemical Name: 3',5'-bis-O-(tert-butyldimethylsilyl)-2'-O-(2-(triphenylmethylthio)ethyl)-N⁶-isobutyryladenosine
• CAS No.: 853748-68-2
• Molecular Formula: C₄₇H₆₅N₅O₅SSi₂
• Molecular Weight: 868.301

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 3',5'-bis-O-(tert-butyldimethylsilyl)-2'-O-(2-(triphenylmethylthio)ethyl)-N⁶-isobutyryladenosine

There total 13 articles about 3',5'-bis-O-(tert-butyldimethylsilyl)-2'-O-(2-(triphenylmethylthio)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: 80.0%

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 (853748-67-1) + triphenylmethanethiol (3695-77-0) → 3',5'-bis-O-(tert-butyldimethylsilyl)-2'-O-(2-(triphenylmethylthio)ethyl)-N6-isobutyryladenosine (853748-68-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 1h;

DOI:10.1021/jo050061l

Reference yield: 73.0%

3',5'-bis-O-(tert-butyldimethylsilyl)-2'-O-(2-hydroxyethyl)-N6-isobutyryladenosine (853748-61-5) + triphenylmethanethiol (3695-77-0) → 3',5'-bis-O-(tert-butyldimethylsilyl)-2'-O-(2-(triphenylmethylthio)ethyl)-N6-isobutyryladenosine (853748-68-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

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) → 3',5'-bis-O-(tert-butyldimethylsilyl)-2'-O-(2-(triphenylmethylthio)ethyl)-N6-isobutyryladenosine (853748-68-2)

Guidance literature:

Multi-step reaction with 11 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

10.1: 73 percent / 4,5-dicyanoimidazole; pyridine / CH₂Cl₂ / 4 h / 20 °C

11.1: 80 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; 4,5-dicyano-1H-imidazole; chloro-trimethyl-silane; sodium azide; tetrabutyl ammonium fluoride; hydrogen; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 11.1: Mitsunobu reaction;

DOI:10.1021/jo050061l

upstream raw materials:

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

triphenylmethanethiol

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

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

Downstream raw materials:

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

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