847659-07-8

Upstream product

• 87199-17-5 4-formylphenylboronic acid, 
• 54-42-2 5-Iodo-2'-deoxyuridine 

Downstream Products

• 847659-10-3 acetic acid 2-acetoxymethyl-5-(5-{4-[1,3-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,5,5-tetramethyl-imidazolidin-2-yl]-phenyl}-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 847659-11-4 5-{4-[1,3-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,5,5-tetramethyl-imidazolidin-2-yl]-phenyl}-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 
• 847659-09-0 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[5-(4-formyl-phenyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester 

Relevant academic research and scientific papers

Nucleotide insertion and bypass synthesis of pyrene- and BODIPY-modified oligonucleotides by DNA polymerases

The chromophores pyrene and bordipyrromethenylbenzene directly linked to the 5-position of uridine are tolerated and recognized as thymine derivatives by DNA polymerases in primer extension experiments. The Royal Society of Chemistry.

Synthesis and spectroscopic characterization of BODIPY-modified uridines as potential fluorescent probes for nucleic acids

BODIPY-modified nucleosides that contain the fluorophore attached to the 5-position of uridine via a short phenylene bridge have been prepared and characterized by optical spectroscopy and by electrochemistry. The target compounds were synthesized using a Pd-catalyzed cross-coupling of 4-formylphenylboronic acid to 5-iodo-2'-desoxyuridine, followed by acidcatalyzed formation of the BODIPY chromophore. The weakly electron-donating ethyl substituents in positions 2 and 6 of the BODIPY dye, shift both the absorption and emission properties of the corresponding modified uridines bathochromically and alter their redox properties. In contrast, exchange of the fluoro ligands at the boron center of the chromophores by methoxy groups does not change the optical properties but increases the electron-rich character of the BODIPY-modified uridines significantly. Georg Thieme Verlag Stuttgart · New York.

Water-Soluble Pd-Imidate Complexes: Broadly Applicable Catalysts for the Synthesis of Chemically Modified Nucleosides via Pd-Catalyzed Cross-Coupling

(Figure Presented) A broadly applicable catalyst system consisting of water-soluble Pd-imidate complexes has been enployed for the Suzuki-Miyaura cross-coupling of four different nucleosides in water under mild conditions. The efficient nature of the catalyst system also allowed its application in developing a microwave-assisted protocol with the purpose of expediting the catalytic reaction. Preliminary mechanistic studies, assisted by catalyst poison tests and stoichiometric tests performed using an electrospray ionization spectrometer, revealed the possible presence of a homotopic catalyst system.

Improved microwave-assisted ligand-free Suzuki-Miyaura cross-coupling of 5-iodo-2′-deoxyuridine in pure water

A facile and efficient methodology for direct synthesis of 5-aryl-2′-deoxyuridines was developed through ligand-free Suzuki-Miyaura cross-coupling reactions starting from totally deprotected 5-iodo-2′- deoxyuridine and various boronic acids. Reactions wer

New, efficient approach for the ligand-free Suzuki-Miyaura reaction of 5-iodo-2′-deoxyuridine in water

A series of 5-aryl-2′-deoxyuridines was prepared, using ligandless Suzuki-Miyaura cross-coupling reactions in neat water, starting from 5-iodo-2′-deoxyuridine as totally deprotected starting material. This ligand-free process gave good to high isolated yi

Highly effective synthesis of C-5-substituted 2-deoxyuridine using Suzuki-Miyaura cross-coupling in water

An efficient protocol to provide a series of C-5-substituted 2-deoxyuridine derivatives using a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction in water has been established. Starting from 2-deoxyuridine derivatives, the target nucleoside analo

Efficient synthesis of unprotected C-5-Aryl/Heteroaryl-2'-deoxyuridine via a suzuki-miyaura reaction in aqueous media

Following our previous results on an environmentally benign one-pot Sonogashira-cyclization protocol to obtain substituted furopyrimidine nucleosides under aqueous conditions, we investigate herein the Suzuki-Miyaura cross-coupling reactions of aryl and h

Synthesis and ESR studies of nitronyl nitroxide-tethered oligodeoxynucleotides

We report on the development of a nucleoside labeled with a nitronyl nitroxide group, NNU, and the synthesis of oligodeoxynucleotides containing NNU. The spin signals of NNU-containing oligodeoxynucleotides varied with the