(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

Base Information

• Chemical Name: (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
• CAS No.: 440115-00-4
• Molecular Formula: C₂₈H₄₁N₃O₅Si₂
• Molecular Weight: 555.822

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 1 articles about (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 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%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + N4-benzoylcytidine (13089-48-0) + (1aR,1bS,4aS,5aR)-1a-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-hexahydro-2-oxa-cyclopropa[a]pentalen-4a-ol (440114-91-0) → (5'R)-N4-benzoyl-1-[5'-O-(tert-butyldimethylsilyl)-2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-α-D-ribofuranosyl]cytosine (440115-08-2) + (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-[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)

Guidance literature:

N₄-benzoylcytidine; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 20 ℃; for 1h;

trimethylsilyl trifluoromethanesulfonate; (1aR,1bS,4aS,5aR)-1a-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-hexahydro-2-oxa-cyclopropa[a]pentalen-4a-ol; In acetonitrile; at 0 - 4 ℃;

DOI:10.1021/ja025569+

Reference yield: 43.0%

(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-[5'-O-(tert-butyldimethylsilyl)-2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-α-D-ribofuranosyl]cytosine (440115-08-2) + (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)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.05h;

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+

upstream raw materials:

trimethylsilyl trifluoromethanesulfonate

N₄-benzoylcytidine

(1aR,1bS,4aS,5aR)-1a-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-hexahydro-2-oxa-cyclopropa[a]pentalen-4a-ol

Downstream raw materials:

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

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

(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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