p-nitrophenyl N⁴-benzoyl-2',5'-dideoxy-5'-(4''-monomethoxytrityl)aminocytidine 3'-carbonate

Base Information

• Chemical Name: p-nitrophenyl N⁴-benzoyl-2',5'-dideoxy-5'-(4''-monomethoxytrityl)aminocytidine 3'-carbonate
• CAS No.: 109205-80-3
• Molecular Formula: C₄₃H₃₇N₅O₉
• Molecular Weight: 767.795
• Mol file: 109205-80-3.mol

Synonyms:p-nitrophenyl N⁴-benzoyl-2',5'-dideoxy-5'-(4''-monomethoxytrityl)aminocytidine 3'-carbonate

Chemical Property of p-nitrophenyl N⁴-benzoyl-2',5'-dideoxy-5'-(4''-monomethoxytrityl)aminocytidine 3'-carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrophenyl N⁴-benzoyl-2',5'-dideoxy-5'-(4''-monomethoxytrityl)aminocytidine 3'-carbonate

There total 3 articles about p-nitrophenyl N⁴-benzoyl-2',5'-dideoxy-5'-(4''-monomethoxytrityl)aminocytidine 3'-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: 67.0%

bis-(p-nitrophenyl) carbonate (5070-13-3) + N4-benzoyl-2',5'-dideoxy-5'-(4''-monomethoxytrityl)aminocytidine (109979-00-2) → p-nitrophenyl N4-benzoyl-2',5'-dideoxy-5'-(4''-monomethoxytrityl)aminocytidine 3'-carbonate (109205-80-3)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; for 2.5h;

DOI:10.1021/jo00228a010

Reference yield:

5'-azido-2',5'-dideoxy-N4-benzoylcytidine (74597-69-6) → p-nitrophenyl N4-benzoyl-2',5'-dideoxy-5'-(4''-monomethoxytrityl)aminocytidine 3'-carbonate (109205-80-3)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 10percent Pd/C / ethanol; dimethylformamide; acetic acid / 18.5 h / 1810.02 Torr

2: pyridine, Et₃N / 4 h

3: 67 percent / Et₃N / dimethylformamide / 2.5 h

With pyridine; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jo00228a010

Reference yield:

5'-amino-N4-benzoyl-2',5'-dideoxycytidine (109978-98-5) → p-nitrophenyl N4-benzoyl-2',5'-dideoxy-5'-(4''-monomethoxytrityl)aminocytidine 3'-carbonate (109205-80-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine, Et₃N / 4 h

2: 67 percent / Et₃N / dimethylformamide / 2.5 h

With pyridine; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jo00228a010

upstream raw materials:

bis-(p-nitrophenyl) carbonate

N⁴-benzoyl-2',5'-dideoxy-5'-(4''-monomethoxytrityl)aminocytidine

5'-amino-N⁴-benzoyl-2',5'-dideoxycytidine

5'-azido-2',5'-dideoxy-N⁴-benzoylcytidine

Downstream raw materials:

[(2R,3S,5R)-5-(4-Benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl]-carbamic acid (2R,3S,5R)-2-aminomethyl-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester; compound with toluene-4-sulfonic acid

4-nitrophenyl N⁴-benzoyl-2',5'-dideoxy-5'-(4''-monomethoxytrityl)aminocytidylyl-(3'-5''-carbamoyl)-5'-amino-N⁴-benzoyl-2',5'-dideoxycytidine 3'-carbonate

N⁴-benzoyl-2',5'-dideoxy-5'-(4''-monomethoxytrityl)aminocytidylyl-(3'-5''-carbamoyl)-5'-amino-N⁴-benzoyl-2',5'-dideoxycytidine

Refernces