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

Base Information

• Chemical Name: N⁴-benzoyl-1-[(2R,3R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)-3-(1-imidazothiocarbonyloxy)tetrahydrofuran-2-yl]cytosine
• CAS No.: 208463-31-4
• Molecular Formula: C₄₀H₄₃N₅O₆S₂Si
• Molecular Weight: 782.029

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about N⁴-benzoyl-1-[(2R,3R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)-3-(1-imidazothiocarbonyloxy)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: 87.0%

1,1'-Thiocarbonyldiimidazole (6160-65-2) + N4-benzoyl-1-[(2R,3R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)-3-hydroxytetrahydrofuran-2-yl]cytosine (208463-27-8) → N4-benzoyl-1-[(2R,3R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)-3-(1-imidazothiocarbonyloxy)tetrahydrofuran-2-yl]cytosine (208463-31-4)

Guidance literature:

In N,N-dimethyl-formamide; for 1.5h; Ambient temperature;

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,3R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)-3-(1-imidazothiocarbonyloxy)tetrahydrofuran-2-yl]cytosine (208463-31-4)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Mitsunobu reaction;

DOI:10.1021/jo0003910

Reference yield:

Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ylmethyl ester (441044-21-9) → N4-benzoyl-1-[(2R,3R,4R,5R)-4-acetylthiomethyl-5-(2-tertbutyldiphenylsilyloxyethyl)-3-(1-imidazothiocarbonyloxy)tetrahydrofuran-2-yl]cytosine (208463-31-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: imidazole; acetic acid / dimethylformamide / 0.83 h

2.1: NaOH / methanol; H₂O

3.1: 21.90 g / 4-dimethylaminopyridine; triethylamine / tetrahydrofuran; methanol / 1.17 h

4.1: N-methyl-N-trimethylsilyltrifluoroacetamide / acetonitrile / 0.5 h

4.2: SnCl₄ / acetonitrile / 0.5 h / 20 °C

5.1: 5.432 g / NaOH / H₂O; methanol / 0.01 h / 20 °C

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

7.1: 83 percent Spectr_. / dimethylformamide / 1.5 h / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; di-isopropyl azodicarboxylate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile; 4.1: Vorbrueggen reaction / 6.1: Mitsunobu reaction;

DOI:10.1021/jo0003910

upstream raw materials:

1,1'-Thiocarbonyldiimidazole

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

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

tert-butylchlorodiphenylsilane

Downstream raw materials:

C₇₁H₇₁N₅O₁₁S₂

C₅₁H₅₅N₅O₁₁S₃

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

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

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