5'-O-monomethoxytrityl-N⁶-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine-3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphate

Base Information

• Chemical Name: 5'-O-monomethoxytrityl-N⁶-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine-3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphate
• CAS No.: 91592-97-1
• Molecular Formula: C₅₃H₄₆Cl₂N₇O₁₃P
• Molecular Weight: 1090.87

Synonyms:5'-O-monomethoxytrityl-N⁶-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine-3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphate

Chemical Property of 5'-O-monomethoxytrityl-N⁶-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine-3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphate

Chemical Property:

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Technology Process of 5'-O-monomethoxytrityl-N⁶-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine-3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphate

There total 11 articles about 5'-O-monomethoxytrityl-N⁶-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine-3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphate 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:

2-(4-nitrophenyl)ethanol (100-27-6) → 5'-O-monomethoxytrityl-N6-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine-3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphate (91592-97-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / toluene; CH₂Cl₂ / 1.) r.t., 1 h; 2.) 50 deg C, 5 h

2: 80 percent / CH₂Cl₂ / 1.) 15 min, 0-5 deg C; 2.) 30 min, r.t.

3: CH₂Cl₂ / 3 h / Heating

4: 1.63 g / half-conc. aq. ammonia / pyridine / 1 h

5: 90 percent / pyridine / 16 h / Ambient temperature

6: 1.) 1,2,4-triazole / 1.) pyridine, 20 min; 2.) pyridine, 1 h; 3.) 16 h, r.t.

With 1,2,4-Triazole; ammonium hydroxide; In pyridine; dichloromethane; toluene;

DOI:10.1016/0040-4020(84)85103-0

Reference yield:

2-(4-nitrophenyl)ethoxycarbonyl chloride (88091-68-3) → 5'-O-monomethoxytrityl-N6-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine-3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphate (91592-97-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / CH₂Cl₂ / 1.) 15 min, 0-5 deg C; 2.) 30 min, r.t.

2: CH₂Cl₂ / 3 h / Heating

3: 1.63 g / half-conc. aq. ammonia / pyridine / 1 h

4: 90 percent / pyridine / 16 h / Ambient temperature

5: 1.) 1,2,4-triazole / 1.) pyridine, 20 min; 2.) pyridine, 1 h; 3.) 16 h, r.t.

With 1,2,4-Triazole; ammonium hydroxide; In pyridine; dichloromethane;

DOI:10.1016/0040-4020(84)85103-0

Reference yield:

1-methyl-3-[2-(4-nitrophenyl)ethoxycarbonyl]imidazolium chloride (88091-70-7) → 5'-O-monomethoxytrityl-N6-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine-3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphate (91592-97-1)

Guidance literature:

Multi-step reaction with 4 steps

1: CH₂Cl₂ / 3 h / Heating

2: 1.63 g / half-conc. aq. ammonia / pyridine / 1 h

3: 90 percent / pyridine / 16 h / Ambient temperature

4: 1.) 1,2,4-triazole / 1.) pyridine, 20 min; 2.) pyridine, 1 h; 3.) 16 h, r.t.

With 1,2,4-Triazole; ammonium hydroxide; In pyridine; dichloromethane;

DOI:10.1016/0040-4020(84)85103-0

upstream raw materials:

2-(4-nitrophenyl)ethanol

2,5-dichlorophenyl phosphorodichloridate

2'-deoxy-5'-O-(4-monomethoxytrityl)-N⁶-[2-(4-nitrophenyl)ethoxycarbonyl]adenosine

9-((2R,4S,5R)-4-Trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamine

Downstream raw materials:

N⁶-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine-3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphate

triethylammonium 5'-O-monomethoxytrityl-N⁶-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine-3'-p-nitrophenylethyl-phosphate

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