2-fluoro-O⁶-<2-(4-nitrophenyl)ethyl>inosine

Base Information

• Chemical Name: 2-fluoro-O⁶-<2-(4-nitrophenyl)ethyl>inosine
• CAS No.: 171284-49-4
• Molecular Formula: C₁₈H₁₈FN₅O₇
• Molecular Weight: 435.369
• Mol file: 171284-49-4.mol

Synonyms:2-fluoro-O⁶-<2-(4-nitrophenyl)ethyl>inosine

Chemical Property of 2-fluoro-O⁶-<2-(4-nitrophenyl)ethyl>inosine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-fluoro-O⁶-<2-(4-nitrophenyl)ethyl>inosine

There total 9 articles about 2-fluoro-O⁶-<2-(4-nitrophenyl)ethyl>inosine 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: 75.0%

2',3',5'-tris(O-triethylsilyl)-N2-(triethylsilyl)-6-O-(4-nitrophenethyl)guanosine (190836-78-3) → 2-fluoro-O6-<2-(4-nitrophenyl)ethyl>inosine (171284-49-4)

Guidance literature:

With tert.-butylnitrite; hydrogen fluoride; In pyridine; at -42 ℃; for 3h;

DOI:10.1021/ja962858n

Reference yield: 72.0%

(2R,3R,4S,5R)-2-(2-amino-6-(4-nitrophenethoxy)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (91592-85-7) → 2-fluoro-O6-<2-(4-nitrophenyl)ethyl>inosine (171284-49-4)

Guidance literature:

With pyridine; hydrogen fluoride; In tetrahydrofuran; 2-Methyl-2-nitropropane; Inert atmosphere;

DOI:10.1021/ja202492e

Reference yield:

2-(4-nitrophenyl)ethanol (100-27-6) → 2-fluoro-O6-<2-(4-nitrophenyl)ethyl>inosine (171284-49-4)

Guidance literature:

Multi-step reaction with 3 steps

1: triphenylphosphine; diethyl azodicarboxylate / dioxane / 20 °C

2: NH₃ / methanol / 20 °C

3: HF/pyridine; tert-butyl nitrite / -50 - -40 °C

With pyridine; tert.-butylnitrite; hydrogen fluoride; ammonia; triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; methanol;

DOI:10.1081/NCN-120028343

upstream raw materials:

(2R,3R,4S,5R)-2-(2-amino-6-(4-nitrophenethoxy)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

2',3',5'-tris(O-triethylsilyl)-N²-(triethylsilyl)-6-O-(4-nitrophenethyl)guanosine

2-(4-nitrophenyl)ethanol

2′,3′,5′-tri-O-acetyl-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

Downstream raw materials:

N₂-cyclopentyl-O₆-(2-(p-nitrophenyl)ethyl)guanosine

N₂-cyclopentyl-5'-O-(4,4'-dimethoxytriphenylmethyl)-O₆-(2-(p-nitrophenyl)ethyl)guanosine

N₂-cyclopentyl-5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(tert-butyldimethylsilyl)-O₆-(2-(p-nitrophenyl)ethyl)guanosine

5'-O-(4,4'-dimethoxytrityl)-3'-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphino]-2'-O-(tert-butyldimethylsilyl)-2-fluoro-6-O-(4-nitrophenethyl)inosine

Refernces

• 1、 Koh, Yung-Hyo,Landesman, Michael B.,Amador, Roberto,Rong, Frank,An, Haoyun,Hong, Zhi,Girardet, Jean-Luc. "Synthesis of Nucleoside Libraries on Solid Support. II. 2,6,8-Trisubstituted Purine Nucleosides Using 8-Bromoguanosine as Precursor". . p. 501 - 507. Retrieved 2007/10/03.
• 2、 Avino,Mayordomo,Espuny,Bach,Eritja. "A convenient method for the preparation of N2,N2-dimethylguanosine". . p. 1613 - 1617. Retrieved 2007/10/02.