Guanosine, 2'-deoxy-6-O-[2-(4-nitrophenyl)ethyl]-, 3',5'-diacetate

Base Information

• Chemical Name: Guanosine, 2'-deoxy-6-O-[2-(4-nitrophenyl)ethyl]-, 3',5'-diacetate
• CAS No.: 108310-92-5
• Molecular Formula: C22H24N6O8
• Molecular Weight: 500.468
• Mol file: 108310-92-5.mol

Synonyms:

Chemical Property of Guanosine, 2'-deoxy-6-O-[2-(4-nitrophenyl)ethyl]-, 3',5'-diacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Guanosine, 2'-deoxy-6-O-[2-(4-nitrophenyl)ethyl]-, 3',5'-diacetate

There total 2 articles about Guanosine, 2'-deoxy-6-O-[2-(4-nitrophenyl)ethyl]-, 3',5'-diacetate 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: 92.0%

2-(4-nitrophenyl)ethanol (100-27-6) + 3',5'-di-O-acetyl-2'-deoxyguanosine (69992-10-5) → 2-amino-6-(2-(p-nitrophenyl)ethyloxy)-9-[2'-deoxy-β-D-erythropentofuranosyl]purine diacetate (108310-92-5)

Guidance literature:

2-(4-nitrophenyl)ethanol; 3',5'-di-O-acetyl-2'-deoxyguanosine; With triphenylphosphine; In 1,4-dioxane; at 20 ℃; for 0.25h;

With azodicarboxylic acid diphenyl ester; In 1,4-dioxane; toluene; at 20 ℃; for 0.5h;

Reference yield:

2'-Deoxyguanosine (961-07-9) → 2-amino-6-(2-(p-nitrophenyl)ethyloxy)-9-[2'-deoxy-β-D-erythropentofuranosyl]purine diacetate (108310-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / pyridine / dimethylformamide / 4 h / 75 °C

2: 1.) PPh₃, 2.) DEAD / 1.) dioxane, 80 deg C, 30 min, 2.) dioxane, 60 deg C, 2 h

With pyridine; triphenylphosphine; diethylazodicarboxylate; In N,N-dimethyl-formamide;

DOI:10.1021/jm970434d

Reference yield: 93.0%

2-amino-6-(2-(p-nitrophenyl)ethyloxy)-9-[2'-deoxy-β-D-erythropentofuranosyl]purine diacetate (108310-92-5) → 3',5'-O-diacetyl-2'-deoxy-2-fluoro-O6-[2-(4-nitrophenyl)ethyl]inosine (169049-77-8)

Guidance literature:

With pyridine; tert.-butylnitrite; hydrogen fluoride; In tert-butyl alcohol; at -50 ℃; for 0.5h;

DOI:10.1002/hlca.201000253

upstream raw materials:

2-(4-nitrophenyl)ethanol

3',5'-di-O-acetyl-2'-deoxyguanosine

2'-Deoxyguanosine

Downstream raw materials:

3',5'-O-diacetyl-2'-deoxy-2-fluoro-O₆-[2-(4-nitrophenyl)ethyl]inosine

3',5'-di-O-acetyl-2'-deoxy-O⁶-[2-(4-nitrophenyl)ethyl]-N²-(phenoxycarbonyl)guanosine

2'-deoxy-O⁶-<2-(4-nitrophenyl)ethyl>guanosine

Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-{2-[(2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonyl)-amino]-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-tetrahydro-furan-3-yl ester