N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}cytosine

Base Information

• Chemical Name: N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}cytosine
• CAS No.: 917376-49-9
• Molecular Formula: C₂₇H₂₇N₅O₁₃
• Molecular Weight: 629.537
• Mol file: 917376-49-9.mol

Synonyms:N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}cytosine

Chemical Property of N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}cytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}cytosine

There total 4 articles about N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}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: 86.0%

N4-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl}cytosine (917376-41-1) → N4-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}cytosine (917376-49-9)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1080/15257770500267113

Reference yield:

1-(3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl)thymine (136317-58-3) → N4-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}cytosine (917376-49-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 18 h / 5 °C

2: 86 percent / AcOH; TBAF*3H₂O / tetrahydrofuran / 12 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1080/15257770500267113

Reference yield:

1-(2,3,5-Tri-O-benzoyl-α-D-arabinofuranosyl)-5-methyluracil (80393-99-3) → N4-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}cytosine (917376-49-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / NaOMe / methanol / 0.75 h

2: 89 percent / pyridine / 15 h / 20 °C

3: 97 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 18 h / 5 °C

4: 86 percent / AcOH; TBAF*3H₂O / tetrahydrofuran / 12 h / 20 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; sodium methylate; acetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1080/15257770500267113

upstream raw materials:

N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl}cytosine

1-(3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl)thymine

1-(2,3,5-Tri-O-benzoyl-α-D-arabinofuranosyl)-5-methyluracil

1-(α-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione

Downstream raw materials:

N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{5-O-(4,4'-dimethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}cytosine

N⁴-[2-(4-nitrophenyl)ethoxycarbonyl]-1-{5-O-(4-monomethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-α-D-arabinofuranosyl}cytosine