Inosine, 2'-deoxy-2-fluoro-6-O-[2-(4-nitrophenyl)ethyl]-

Base Information

• Chemical Name: Inosine, 2'-deoxy-2-fluoro-6-O-[2-(4-nitrophenyl)ethyl]-
• CAS No.: 132183-39-2
• Molecular Formula: C18H18FN5O6
• Molecular Weight: 419.369
• Mol file: 132183-39-2.mol

Synonyms:

Chemical Property of Inosine, 2'-deoxy-2-fluoro-6-O-[2-(4-nitrophenyl)ethyl]-

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Inosine, 2'-deoxy-2-fluoro-6-O-[2-(4-nitrophenyl)ethyl]-

There total 18 articles about Inosine, 2'-deoxy-2-fluoro-6-O-[2-(4-nitrophenyl)ethyl]- 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: 90.0%

3′,5′-O-bis(tert-butyldimethylsilyl)-O6-(p-nitrophenylethyl)-2′-deoxy-2-fluoroguanosine (190506-33-3) → 2-fluoro-O6-(2-(p-nitrophenyl)ethyl)-2'-deoxyinosine (132183-39-2)

Guidance literature:

With triethylamine trihydrofluoride; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1016/S0040-4039(97)00540-6

Reference yield:

2-(4-nitrophenyl)ethanol (100-27-6) → 2-fluoro-O6-(2-(p-nitrophenyl)ethyl)-2'-deoxyinosine (132183-39-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / PPh₃; DEAD / dioxane / 24 h

2: 75 percent / poly[4-vinylpyridinium poly(hydrogen fluoride)]; t-BuONO / toluene / -65 - -5 °C

3: 88 percent / TEA*3HF / tetrahydrofuran / 17 h / 20 °C

With tert.-butylnitrite; poly[4-vinylpyridinium poly(hydrogen fluoride)]; triethylamine tris(hydrogen fluoride); triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; toluene;

DOI:10.1002/1521-3765(20001117)6:22<4188::AID-CHEM4188>3.0.CO;2-N

Reference yield:

2'-Deoxyguanosine (961-07-9) → 2-fluoro-O6-(2-(p-nitrophenyl)ethyl)-2'-deoxyinosine (132183-39-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / imidazole / dimethylformamide / 24 h / 20 °C

2: 80 percent / PPh₃; DEAD / dioxane / 24 h

3: 75 percent / poly[4-vinylpyridinium poly(hydrogen fluoride)]; t-BuONO / toluene / -65 - -5 °C

4: 88 percent / TEA*3HF / tetrahydrofuran / 17 h / 20 °C

With 1H-imidazole; tert.-butylnitrite; poly[4-vinylpyridinium poly(hydrogen fluoride)]; triethylamine tris(hydrogen fluoride); triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/1521-3765(20001117)6:22<4188::AID-CHEM4188>3.0.CO;2-N

upstream raw materials:

3′,5′-O-bis(tert-butyldimethylsilyl)-O⁶-(p-nitrophenylethyl)-2′-deoxy-2-fluoroguanosine

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

6-O-(4-nitrophenylethyl)-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyguanosine

2-(4-nitrophenyl)ethanol

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-6-O-(4-nitrophenylethyl)-2-N-(4,9,13-triazatridecane-1-yl)-2'-deoxyguanosine

5'-O-(4,4'-dimethoxytrityl)-6-O-(4-nitrophenylethyl)-2-N-[tris(N,N',N''-trifluoroacetyl)-4,9,13-triazatridecane-1-yl]-2'-deoxyguanosine

2'-Deoxy-5'-(p-dimethoxytrityl)-N²-(1-pyrenylmethyl)guanosine

(+/-)-N²-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)guanosine phosphoramidite

Refernces

• 1、 Kawashima, Etsuko,Nakanishi, Yasuhiro,Terui, Yusuke,Tomitori, Hideyuki,Kashiwagi, Keiko,Ohba, Yusuke,Kamaike, Kazuo. "Synthesis and evaluation of pyrrole polyamide-2′-deoxyguanosine 5′-phosphate hybrid". . p. 196 - 205. Retrieved 2013/06/04.
• 2、 Godzina, Przemyslaw,Adrych-Rozek, Katarzyna,Markiewicz, Wojciech T.. "Synthetic oligonucleotide combinatorial libraries. 3. Synthesis of polyaminonucleosides". . p. 2397 - 2414. Retrieved 2007/10/03.