Thymidine, 5'-[2-(2-nitrophenyl)propyl carbonate]

Base Information

• Chemical Name: Thymidine, 5'-[2-(2-nitrophenyl)propyl carbonate]
• CAS No.: 189216-59-9
• Molecular Formula: C20H23N3O9
• Molecular Weight: 449.417
• Mol file: 189216-59-9.mol

Synonyms:

Chemical Property of Thymidine, 5'-[2-(2-nitrophenyl)propyl carbonate]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Thymidine, 5'-[2-(2-nitrophenyl)propyl carbonate]

There total 13 articles about Thymidine, 5'-[2-(2-nitrophenyl)propyl carbonate] 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: 82.0%

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) + 2-(o-nitrophenyl)prop-1-yl p-nitrophenyl carbonate → 3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}thymidine (298699-71-5) + 5'-O-[2-(o-nitrophenyl)prop-1-yloxycarbonyl]thymidine (189216-59-9) + thymidine 3',5'-bis[2-(2-nitrophenyl)propyl carbonate]

Guidance literature:

With pyridine; triethylamine; In dichloromethane; at 0 - 25 ℃; for 14h;

Reference yield:

2-ethyl-1,3,5-trinitrobenzene (13985-60-9) → 5'-O-[2-(o-nitrophenyl)prop-1-yloxycarbonyl]thymidine (189216-59-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 48 percent / ammonia; H₂S / dioxane / 35 - 40 °C

2.1: NaNO₂; AcOH; H₂SO₄ / H₂O / 1 h / 20 - 25 °C

2.2: 76 percent / Cu₂O / ethanol; H₂O / 1.5 h / 20 °C

3.1: 81 percent / formic acid; Et₃N / Pd/C / acetonitrile / 0.42 h / Heating

4.1: aq. HBr; NaNO₂ / H₂O / 0.17 h / 0 °C

4.2: urea / H₂O / 0.08 h

4.3: 87 percent / CuSO₄*5H₂O; Cu; aq. HBr / H₂O / 1 h / 80 °C

5.1: 2 percent / NaCN / dimethylsulfoxide / 2 h / 20 °C

6.1: 100 percent / Et₃N / tetrahydrofuran / 1 h / 0 °C

7.1: 0.359 g / pyridine / CH₂Cl₂ / 5 h / -50 - -20 °C

With pyridine; formic acid; sulfuric acid; hydrogen sulfide; sodium cyanide; ammonia; hydrogen bromide; acetic acid; triethylamine; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1002/hlca.200490060

Reference yield:

2-ethyl-1,3-dinitrobenzene (13985-56-3) → 5'-O-[2-(o-nitrophenyl)prop-1-yloxycarbonyl]thymidine (189216-59-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 81 percent / formic acid; Et₃N / Pd/C / acetonitrile / 0.42 h / Heating

2.1: aq. HBr; NaNO₂ / H₂O / 0.17 h / 0 °C

2.2: urea / H₂O / 0.08 h

2.3: 87 percent / CuSO₄*5H₂O; Cu; aq. HBr / H₂O / 1 h / 80 °C

3.1: 2 percent / NaCN / dimethylsulfoxide / 2 h / 20 °C

4.1: 100 percent / Et₃N / tetrahydrofuran / 1 h / 0 °C

5.1: 0.359 g / pyridine / CH₂Cl₂ / 5 h / -50 - -20 °C

With pyridine; formic acid; sodium cyanide; hydrogen bromide; triethylamine; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1002/hlca.200490060

upstream raw materials:

2-(2-nitrophenyl)propyl chloroformate

thymidine

2-ethyl-1,3,5-trinitrobenzene

2-ethyl-1,3-dinitrobenzene

Downstream raw materials:

thymidine