adenosine 3',5'-cyclic([Rp]-{4-[N,N-bis(carboxymethyl)carbamoyl]-2-nitrophenyl}methyl) phosphate

Base Information

• Chemical Name: adenosine 3',5'-cyclic([Rp]-{4-[N,N-bis(carboxymethyl)carbamoyl]-2-nitrophenyl}methyl) phosphate
• CAS No.: 438468-94-1
• Molecular Formula: C₂₂H₂₂N₇O₁₃P
• Molecular Weight: 623.43

Synonyms:adenosine 3',5'-cyclic([Rp]-{4-[N,N-bis(carboxymethyl)carbamoyl]-2-nitrophenyl}methyl) phosphate

Chemical Property of adenosine 3',5'-cyclic([Rp]-{4-[N,N-bis(carboxymethyl)carbamoyl]-2-nitrophenyl}methyl) phosphate

Chemical Property:

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Technology Process of adenosine 3',5'-cyclic([Rp]-{4-[N,N-bis(carboxymethyl)carbamoyl]-2-nitrophenyl}methyl) phosphate

There total 2 articles about adenosine 3',5'-cyclic([Rp]-{4-[N,N-bis(carboxymethyl)carbamoyl]-2-nitrophenyl}methyl) 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: 87.0%

adenosine 3',5'-cyclic([Rp]-{4-[N,N-bis(2-(trimethylsilyl)ethoxycarbonylmethyl)carbamoyl]-2-nitrophenyl}methyl) phosphate (438469-01-3) → adenosine 3',5'-cyclic([Rp]-{4-[N,N-bis(carboxymethyl)carbamoyl]-2-nitrophenyl}methyl) phosphate (438468-94-1)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 0.5h;

DOI:10.1021/jo020040g

Reference yield:

N-(4-(bromomethyl)-3-nitrobenzoyl)iminodiacetic acid bis[2-(trimethylsilyl)ethyl] ester (438468-98-5) → adenosine 3',5'-cyclic([Rp]-{4-[N,N-bis(carboxymethyl)carbamoyl]-2-nitrophenyl}methyl) phosphate (438468-94-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₃NH / ethanol

1.2: 53 mg / Na₂CO₃ / N,N-dimethyl-acetamide / 1 h / 80 °C

2.1: 87 percent / TFA / 0.5 h / 20 °C

With trifluoroacetic acid; In ethanol;

DOI:10.1021/jo020040g

Reference yield:

adenosine 3',5'-cyclic([Rp]-{4-[N,N-bis(carboxymethyl)carbamoyl]-2-nitrophenyl}methyl) phosphate (438468-94-1) → [carboxymethyl-(4-hydroxymethyl-3-nitro-benzoyl)-amino]-acetic acid + (2R,4aR,6R,7R,7aS)-6-(6-Amino-purin-9-yl)-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

Guidance literature:

In water; at 22 ℃; pH=7.00; Further Variations:; pH-values; Kinetics;

DOI:10.1021/jo020040g

upstream raw materials:

adenosine 3',5'-cyclic([Rp]-{4-[N,N-bis(2-(trimethylsilyl)ethoxycarbonylmethyl)carbamoyl]-2-nitrophenyl}methyl) phosphate

N-(4-(bromomethyl)-3-nitrobenzoyl)iminodiacetic acid bis[2-(trimethylsilyl)ethyl] ester

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