N2-Isobutyryl-2'-Fluoro-2'-deoxyguanosine

Base Information

• Chemical Name: N2-Isobutyryl-2'-Fluoro-2'-deoxyguanosine
• CAS No.: 80681-25-0
• Molecular Formula: C14H18FN5O5
• Molecular Weight: 355.326
• Mol file: 80681-25-0.mol

Synonyms:IBU-2'-F-DG;

Chemical Property of N2-Isobutyryl-2'-Fluoro-2'-deoxyguanosine

Chemical Property:

• PKA: 9.16±0.20(Predicted)
• PSA: 142.36000
• Density: 1.78±0.1 g/cm3(Predicted)
• LogP: -0.62420

Purity/Quality:

98%, ^*data from raw suppliers

N-(9-((2R,3R,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N2-Isobutyryl-2'-Fluoro-2'-deoxyguanosine

There total 19 articles about N2-Isobutyryl-2'-Fluoro-2'-deoxyguanosine 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: 57.6%

N2-isobutyryl-3'-O,5'-O-bis(tetrahydrofuranyl)-2'-deoxy-2'-fluoroguanosine (78842-12-3) → 2’-fluoro-N2-isobutyryl-2’-deoxyguanosine (80681-25-0)

Guidance literature:

With acetic acid; for 12h; Ambient temperature;

Reference yield: 41.0%

N2-isobutyryl-9-(2-fluoro-3,5-di-O-tetrahydropyran-2-yl-β-D-arabinofuranosyl)guanine (146954-69-0) → 2’-fluoro-N2-isobutyryl-2’-deoxyguanosine (80681-25-0)

Guidance literature:

With Dowex 50W x 2-100; In methanol; at 23 ℃; for 1h;

DOI:10.1021/jm00059a007

Reference yield:

9-β-D-arabinofuranosylguanine (38819-10-2) → 2’-fluoro-N2-isobutyryl-2’-deoxyguanosine (80681-25-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) TMSCl, pyridine, 3.) NH₄OH

2: TsOH / dioxane

3: DMAP / CH₂Cl₂

4: TBAF / tetrahydrofuran

5: Dowex-50 / methanol

With pyridine; dmap; ammonium hydroxide; chloro-trimethyl-silane; Dowex-50; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1080/07328319708006246

upstream raw materials:

N²-isobutyryl-3'-O,5'-O-bis(tetrahydrofuranyl)-2'-deoxy-2'-fluoroguanosine

N²-isobutyryl-9-(2-fluoro-3,5-di-O-tetrahydropyran-2-yl-β-D-arabinofuranosyl)guanine

9-β-D-arabinofuranosylguanine

2,6-diamino-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine

Downstream raw materials:

N²-isobutyryl-5'-O-monomethoxytrityl-2'-deoxy-2'-fluoroguanosine

2'-deoxy-2'-fluoroguanosine

N-(9-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide

Refernces

• 1、 Ross, Bruce S.,Springer, Robert H.,Sprankle, Kelly G.,Vasquez, Guillermo. "An efficient and scalable synthesis of arabinosylguanine and 2′-deoxy-2′-fluoro-guanosine". . p. 1645 - 1647. Retrieved 2007/10/03.
• 2、 Ikehara, Morio,Imura, Junko. "Studies on Nucleosides and Nucleotides. LXXXVIII. Synthesis of a Non-hydrolyzable Substrate Analog of Ribonuclease Tl, 2'-Deoxy-2'-fluoroguanylyl-(3'-5')-uridine". . p. 2408 - 2412. Retrieved 2007/10/02.