N⁴-benzoyl-1-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]-cytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]-cytosine
• CAS No.: 181423-12-1
• Molecular Formula: C₅₈H₅₅N₃O₁₂Si
• Molecular Weight: 1014.17

Synonyms:N⁴-benzoyl-1-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]-cytosine

Chemical Property of N⁴-benzoyl-1-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]-cytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of N⁴-benzoyl-1-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]-cytosine

There total 3 articles about N⁴-benzoyl-1-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]-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: 71.0%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + N-(1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide (139244-40-9) → N4-benzoyl-1-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]-cytosine (181423-12-1)

Guidance literature:

With tin(IV) chloride; In 1,2-dichloro-ethane; at 0 ℃; for 0.666667h;

DOI:10.1080/07328319608002433

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → N4-benzoyl-1-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]-cytosine (181423-12-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / imidazole / pyridine / 5 h / 20 °C

2: 71 percent / SnCl₄ / 1,2-dichloro-ethane / 0.67 h / 0 °C

With 1H-imidazole; tin(IV) chloride; In pyridine; 1,2-dichloro-ethane;

DOI:10.1080/07328319608002433

Reference yield:

N4-benzoyl-2'-deoxycytidine (4836-13-9) → N4-benzoyl-1-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]-cytosine (181423-12-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / imidazole / pyridine / 5 h / 20 °C

2: 71 percent / SnCl₄ / 1,2-dichloro-ethane / 0.67 h / 0 °C

With 1H-imidazole; tin(IV) chloride; In pyridine; 1,2-dichloro-ethane;

DOI:10.1080/07328319608002433

upstream raw materials:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

N-(1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

N₄-benzoyl-2'-deoxycytidine

tert-butylchlorodiphenylsilane

Downstream raw materials:

N⁴-benzoyl-1-[3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]-cytosine

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