8-BROMO-N2-(DIMETHYLAMINOMETHYLIDENE)-2'-DEOXYGUANOSINE

Base Information

• Chemical Name: 8-BROMO-N2-(DIMETHYLAMINOMETHYLIDENE)-2'-DEOXYGUANOSINE
• CAS No.: 717876-75-0
• Molecular Formula: C₁₃H₁₇BrN₆O₄
• Molecular Weight: 401.22
• Mol file: 717876-75-0.mol

Synonyms:

Chemical Property of 8-BROMO-N2-(DIMETHYLAMINOMETHYLIDENE)-2'-DEOXYGUANOSINE

Chemical Property:

• PSA: 128.86000
• LogP: -0.25580

Purity/Quality:

97% ^*data from raw suppliers

8-Bromo-N2-(dimethylaminomethylidene)-2’-deoxyguanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 8-Bromo-N2-(dimethylaminomethylidene)-2’-deoxyguanosine is a 2’-Deoxyguanosine derivative which possesses solvatochromic fluorescent activity.

Technology Process of 8-BROMO-N2-(DIMETHYLAMINOMETHYLIDENE)-2'-DEOXYGUANOSINE

There total 2 articles about 8-BROMO-N2-(DIMETHYLAMINOMETHYLIDENE)-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: 100.0%

8-bromo-2'-deoxyguanosine (13389-03-2) + N,N-dimethylformamide diethyl diacetal (1188-33-6) → N'-[8-Bromo-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-N,N-dimethyl-formamidine (717876-75-0)

Guidance literature:

In methanol; at 55 ℃; for 6h;

DOI:10.1016/j.tetlet.2010.03.012

Reference yield: 98.0%

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + 8-bromo-2'-deoxyguanosine (13389-03-2) → N'-[8-Bromo-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-N,N-dimethyl-formamidine (717876-75-0)

Guidance literature:

In methanol; at 60 ℃; for 12h;

DOI:10.1016/j.bmcl.2010.11.129

Reference yield:

N'-[8-Bromo-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-N,N-dimethyl-formamidine (717876-75-0) → N(2)-dimethylaminomethylene-8-(prop-1-ynyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine (204582-55-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine, DMAP / 1 h

2: 77 percent / CuI, NEt₃ / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / dimethylformamide / 4 h

With pyridine; dmap; copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide;

DOI:10.1039/a707031d

upstream raw materials:

N,N-dimethyl-formamide dimethyl acetal

8-bromo-2'-deoxyguanosine

N,N-dimethylformamide diethyl diacetal

Downstream raw materials:

5'-O-(dimethoxytrityl)-N²-(N,N-dimethylaminomethyliden)-8-bromo-2'-deoxyguanosine

N⁽²⁾-dimethylaminomethylene-8-(prop-1-ynyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine

C₅₃H₆₁N₈O₈P

C₄₄H₄₄N₆O₇