N⁴-benzoyl-1-[(2R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)tetrahydrofuran-2-yl]cytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-[(2R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)tetrahydrofuran-2-yl]cytosine
• CAS No.: 208463-36-9
• Molecular Formula: C₃₆H₄₁N₃O₅SSi
• Molecular Weight: 655.89

Synonyms:N⁴-benzoyl-1-[(2R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)tetrahydrofuran-2-yl]cytosine

Chemical Property of N⁴-benzoyl-1-[(2R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)tetrahydrofuran-2-yl]cytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of N⁴-benzoyl-1-[(2R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)tetrahydrofuran-2-yl]cytosine

There total 9 articles about N⁴-benzoyl-1-[(2R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)tetrahydrofuran-2-yl]cytosine 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: 86.0%

N4-benzoyl-1-[(2R,3R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)-3-(1-imidazothiocarbonyloxy)tetrahydrofuran-2-yl]cytosine (208463-31-4) → N4-benzoyl-1-[(2R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)tetrahydrofuran-2-yl]cytosine (208463-36-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 0.0333333h; Heating;

DOI:10.1080/07328319808003461

Reference yield:

N4-benzoyl-1-[(2R,3R,4R,5R)-5-(2-tertbutyldiphenylsilyloxyethyl)-3-hydroxy-4-hydroxymethyltetrahydrofuran-2-yl]cytosine (208463-23-4) → N4-benzoyl-1-[(2R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)tetrahydrofuran-2-yl]cytosine (208463-36-9)

Guidance literature:

Multi-step reaction with 3 steps

1: diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / -20 - 20 °C

2: 83 percent Spectr_. / dimethylformamide / 1.5 h / 20 °C

3: 86 percent / Bu₃SnH; azobisisobutyronitrile / toluene / 0.03 h / Heating

With 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tri-n-butyl-tin hydride; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 1: Mitsunobu reaction / 3: Barton deoxygenation;

DOI:10.1021/jo0003910

Reference yield:

N4-benzoyl-1-[(2R,3R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)-3-hydroxytetrahydrofuran-2-yl]cytosine (208463-27-8) → N4-benzoyl-1-[(2R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)tetrahydrofuran-2-yl]cytosine (208463-36-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent Spectr_. / dimethylformamide / 1.5 h / 20 °C

2: 86 percent / Bu₃SnH; azobisisobutyronitrile / toluene / 0.03 h / Heating

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In N,N-dimethyl-formamide; toluene; 2: Barton deoxygenation;

DOI:10.1021/jo0003910

upstream raw materials:

N⁴-benzoyl-1-[(2R,3R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)-3-(1-imidazothiocarbonyloxy)tetrahydrofuran-2-yl]cytosine

Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ylmethyl ester

tert-butylchlorodiphenylsilane

N⁴-benzoyl-1-[(2R,3R,4R,5R)-5-(2-tertbutyldiphenylsilyloxyethyl)-3-hydroxy-4-hydroxymethyltetrahydrofuran-2-yl]cytosine

Downstream raw materials:

N-{1-[(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methylsulfanylmethyl]-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

Methanesulfonic acid 2-{(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[bis-(4-methoxy-phenyl)-phenyl-methylsulfanylmethyl]-tetrahydro-furan-2-yl}-ethyl ester

N-(1-{4-[bis-(4-methoxy-phenyl)-phenyl-methylsulfanylmethyl]-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide

C₅₁H₅₅N₅O₁₁S₃

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