N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine

Base Information

• Chemical Name: N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine
• CAS No.: 142068-16-4
• Molecular Formula: C₂₂H₂₉N₃O₄Si
• Molecular Weight: 427.575
• Mol file: 142068-16-4.mol

Synonyms:N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine

Chemical Property of N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine

There total 3 articles about N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine 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: 65.0%

N4-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)thiocarbonyl>cytidine (142102-28-1) → N4-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine (142068-16-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 1h; Heating;

DOI:10.1021/jm00093a003

Reference yield:

Dithiocarbonic acid O-[(2R,3R,4R,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-dithiocarboxyoxy-tetrahydro-furan-3-yl] ester → N4-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine (142068-16-4)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 0.5 h

2: 65 percent / tri-n-butyltin hydride, azobisisobutyronitrile / toluene / 1 h / Heating

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; toluene;

DOI:10.1021/jm00093a003

Reference yield:

N4-benzoyl-5'-O-(tert-butyldimethylsilyl)cytidine (72409-20-2) → N4-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine (142068-16-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH, imidazole / 1.) THF, 45 min, 2.) THF, 30 min

2: tetrahydrofuran / 0.5 h

3: 65 percent / tri-n-butyltin hydride, azobisisobutyronitrile / toluene / 1 h / Heating

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; In tetrahydrofuran; toluene;

DOI:10.1021/jm00093a003

upstream raw materials:

N⁴-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)thiocarbonyl>cytidine

N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)cytidine

Downstream raw materials:

Phosphoric acid (2S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester phenyl ester; compound with ammonia

Phenyl-phosphonothioic acid O-[(2S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl] ester; compound with ammonia

Phenyl-phosphonic acid mono-[(2S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl] ester; compound with ammonia

N⁴-benzoyl-2',3'-didehydro-2',3'-dideoxycytidine 5'-dimethyl phosphate

Refernces