121409-45-8Relevant academic research and scientific papers
Oligonucleotide synthesis involving deprotection of amidine-type protecting groups for nucleobases under acidic conditions
Ohkubo, Akihiro,Kuwayama, Yasukazu,Nishino, Yudai,Tsunoda, Hirosuke,Seio, Kohji,Sekine, Mitsuo
supporting information; scheme or table, p. 2496 - 2499 (2010/08/07)
Amidine-type protecting groups, i.e., N,N-dimethylformamidine (dmf) and N,N-dibutylformamidine (dbf) groups, introduced into nucleobases were rapidly removed under mild acidic conditions using imidazolium triflate (IMT) or 1-hydroxybenztriazole (HOBt). This new deprotection strategy allowed a 2′-O-methyl-RNA derivative bearing a base-labile group to be efficiently synthesized using a silyl-type linker. It was also found that our new method could be applied to the synthesis of an unmodified RNA oligomer.
Nucleic acid related compounds. 127. Selective N-deacylation of N,O-peracylated nucleosides in superheated methanol
Nowak, Ireneusz,Conda-Sheridan, Martin,Robins, Morris J.
, p. 7455 - 7458 (2007/10/03)
Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath ≥ 105 °C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.
(S,S)-(+)-pseudoephedrine as chiral auxiliary in asymmetric aza-Michael reactions. Unexpected selectivity change when manipulating the structure of the auxiliary
Etxebarria, Juan,Vicario, Jose L.,Badia, Dolores,Carrillo, Luisa,Ruiz, Nerea
, p. 8790 - 8800 (2007/10/03)
The asymmetric aza-Michael reaction of metal benzylamides to α,β-unsaturated amides derived from the chiral amino alcohol (S,S)-(+)-pseudoephedrine has been studied in detail. A deep study of the most important experimental parameters (solvent, temperatur
THE SYNTHESIS OF 2'-DEOXYADENOSINE VIA STEREOSPECIFIC COUPLING REACTION
Kawakami, Hiroshi,Matsushita, Hajime,Naoi, Yoshitake,Itoh, Kazuo,Yoshikoshi, Hajime
, p. 235 - 238 (2007/10/02)
The coupling reaction of the sodium salt of adenine, which could be easily prepared by deprotonation with sodium hydroxide or sodium methoxide, with 1-α-chloro-2-deoxyribose derivative proceeded in a good stereospecific manner in acetone as a solvent to give the β-anomer of the corresponding acylated adenosine.
