(5'R)-N⁴-benzoyl-1-[2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-β-D-ribofuranosyl]cytosine

Base Information

• Chemical Name: (5'R)-N⁴-benzoyl-1-[2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-β-D-ribofuranosyl]cytosine
• CAS No.: 440115-16-2
• Molecular Formula: C₁₉H₁₉N₃O₅
• Molecular Weight: 369.377

Synonyms:(5'R)-N⁴-benzoyl-1-[2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-β-D-ribofuranosyl]cytosine

Chemical Property of (5'R)-N⁴-benzoyl-1-[2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-β-D-ribofuranosyl]cytosine

Chemical Property:

Purity/Quality:

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Technology Process of (5'R)-N⁴-benzoyl-1-[2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-β-D-ribofuranosyl]cytosine

There total 2 articles about (5'R)-N⁴-benzoyl-1-[2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-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: 90.0%

(5'R)-N4-benzoyl-1-[5'-O-(tert-butyldimethylsilyl)-2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-β-D-ribofuranosyl]cytosine (440115-04-8) → (5'R)-N4-benzoyl-1-[2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-β-D-ribofuranosyl]cytosine (440115-16-2)

Guidance literature:

With triethylamine hydrofluoride; In tetrahydrofuran; for 9h;

DOI:10.1021/ja025569+

Reference yield:

(5'R)-N4-benzoyl-1-[3'-O-trimethylsilyl-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-D-ribofuranosyl]cytosine (440115-00-4) → (5'R)-N4-benzoyl-1-[2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-β-D-ribofuranosyl]cytosine (440115-16-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / Bu₄NF / tetrahydrofuran / 0.05 h

2: 90 percent / HF*Et₃N / tetrahydrofuran / 9 h

With tetrabutyl ammonium fluoride; triethylamine hydrofluoride; In tetrahydrofuran;

DOI:10.1021/ja025569+

Reference yield: 87.0%

4,4’-dimethoxytrityl trifluoromethanesulfonate (239808-67-4) + (5'R)-N4-benzoyl-1-[2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-β-D-ribofuranosyl]cytosine (440115-16-2) → (5'R)-N4-benzoyl-1-[5'-O-(4,4'-dimethoxytriphenyl)methyl-2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-β-D-ribofuranosyl]cytosine (440115-12-8)

Guidance literature:

With pyridine; for 12h;

DOI:10.1021/ja025569+

upstream raw materials:

(5'R)-N⁴-benzoyl-1-[5'-O-(tert-butyldimethylsilyl)-2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-β-D-ribofuranosyl]cytosine

(5'R)-N⁴-benzoyl-1-[3'-O-trimethylsilyl-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-D-ribofuranosyl]cytosine

Downstream raw materials:

(5'R)-N⁴-benzoyl-1-[5'-O-(4,4'-dimethoxytriphenyl)methyl-2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-β-D-ribofuranosyl]cytosine

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