N⁴-2-(4-nitrophenyl)ethoxycarbonyl-3'-deoxycytidi

Base Information

• Chemical Name: N⁴-2-(4-nitrophenyl)ethoxycarbonyl-3'-deoxycytidi
• CAS No.: 161110-15-2
• Molecular Formula: C₁₈H₂₀N₄O₈
• Molecular Weight: 420.379
• Mol file: 161110-15-2.mol

Synonyms:

Chemical Property of N⁴-2-(4-nitrophenyl)ethoxycarbonyl-3'-deoxycytidi

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁴-2-(4-nitrophenyl)ethoxycarbonyl-3'-deoxycytidi

There total 28 articles about N⁴-2-(4-nitrophenyl)ethoxycarbonyl-3'-deoxycytidi 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:

5'-O-trityluridine (6554-10-5) → N4-2-(4-nitrophenyl)ethoxycarbonyl-3'-deoxycytidi (161110-15-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 43 percent / DBU / acetonitrile / 15 h / Ambient temperature

2: 65 percent / DMAP / acetonitrile / 20 h / Ambient temperature

3: AIBN, Bu₃SnH / toluene / 3 h / 85 °C

4: TBAF / tetrahydrofuran / 4 h / 75 °C

5: 81 percent / ZnBr₂ / CH₂Cl₂; methanol / 0.33 h

6: 80 percent / pyridine / 20 h / Ambient temperature

7: 69 percent / o-chlorophenylphosphorodichloridate / pyridine / 48 h / Ambient temperature

8: 75 percent / NH₄OH / dioxane / 2.5 h / Ambient temperature

9: 82 percent / NaOEt / 24 h / Ambient temperature

10: 1.) hexamethyldisilazane, 2.) Et₃N / 1.) dioxane, reflux, 12 h, 2.) CH₂Cl₂, MeOH, RT, 12 h

With pyridine; dmap; ammonium hydroxide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium ethanolate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; zinc dibromide; 2-chlorophenyl dichlorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; toluene; acetonitrile;

DOI:10.1080/15257779408012162

Reference yield:

uridine (58-96-8) → N4-2-(4-nitrophenyl)ethoxycarbonyl-3'-deoxycytidi (161110-15-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 50 percent / DBU / acetonitrile / 2 h / Ambient temperature

2: 81 percent / DMAP / acetonitrile / 20 h / Ambient temperature

3: AIBN, Bu₃SnH / toluene / 6 h / 75 °C

4: TBAF / tetrahydrofuran / 1 h

5: 80 percent / pyridine / 20 h / Ambient temperature

6: 69 percent / o-chlorophenylphosphorodichloridate / pyridine / 48 h / Ambient temperature

7: 75 percent / NH₄OH / dioxane / 2.5 h / Ambient temperature

8: 82 percent / NaOEt / 24 h / Ambient temperature

9: 1.) hexamethyldisilazane, 2.) Et₃N / 1.) dioxane, reflux, 12 h, 2.) CH₂Cl₂, MeOH, RT, 12 h

With pyridine; dmap; ammonium hydroxide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium ethanolate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; 2-chlorophenyl dichlorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; toluene; acetonitrile;

DOI:10.1080/15257779408012162

Reference yield:

α-D-xylofuranose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → N4-2-(4-nitrophenyl)ethoxycarbonyl-3'-deoxycytidi (161110-15-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 66 percent / conc. H₂SO₄ / 3 h

2: 66 percent / pyridine / 1 h / 0 °C

3: DMAP / acetonitrile / 2 h / Ambient temperature

4: 72 percent / AIBN, Bu₃SnH / toluene / 6 h / 80 °C

5: HCOOH / 2 h / 50 °C

6: pyridine / 2 h / Ambient temperature

7: 1.) hexamethyldisilazane, (NH₄)2SO₄, 2.) trimethylsilyl triflate / 1.) reflux, 1,2-dichloroethane, RT, 1.5 h

8: 72 percent / NaOEt / 24 h / Ambient temperature

9: 1.) hexamethyldisilazane, 2.) Et₃N / 1.) dioxane, reflux, 12 h, 2.) CH₂Cl₂, MeOH, RT, 12 h

With dmap; ammonium sulfate; formic acid; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; sulfuric acid; tri-n-butyl-tin hydride; sodium ethanolate; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In pyridine; toluene; acetonitrile;

DOI:10.1080/15257779408012162

upstream raw materials:

1-methyl-3-[2-(4-nitrophenyl)ethoxycarbonyl]imidazolium chloride

3'-deoxycytidine

α-D-xylofuranose

3'-deoxyuridine

Refernces