4785-07-3Relevant academic research and scientific papers
Chemical synthesis of RNA via 2′-O-cyanoethylated intermediates
Saneyoshi, Hisao,Ando, Kaori,Seio, Kohji,Sekine, Mitsuo
, p. 11195 - 11203 (2008/03/11)
It was found that 2′-O-cyanoethyl group could be removed from 2′-O-cyanoethylated ribonucleoside derivatives by treatment with Bu4NF. This finding was successfully applied to the synthesis of oligoribonucleotides via their 2′-O-cyanoethylated derivatives as key intermediates where a cyanoethyl group was used as the 2′-hydroxyl protecting group. The rate of condensation using this protecting group in the presence of various activators was generally faster than that observed when a TBDMS group was used as the protecting group.
Some observations relating to the use of 1-aryl-4-alkoxypiperidin-4-yl groups for the protection of the 2′-hydroxy functions in the chemical synthesis of oligoribonucleotides
Lloyd, Wayne,Reese, Colin B.,Song, Quanlai,Vandersteen, Anthony M.,Visintin, Cristina,Zhang, Pei-Zhou
, p. 165 - 176 (2007/10/03)
The comparative rates of acid-catalysed removal often 1-aryl-4-methoxypiperidin-4-yl 8 (R = Me) [including the previously reported Ctmp 5 and Fpmp 6] protecting groups for the 2′-hydroxy functions in oligoribonucleotide synthesis are discussed. These studies have led to the development of the 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl (Cpep) protecting group 8 (R = Et, R1 = R2 = H, R3 = Cl) which is both more stable than the Ctmp and Fpmp groups at pH 0.5 and more labile at pH 3.75. The influence of the ribonucleoside aglycone on the stability of the 2′-O-Fpmp and 2′-O-Ctmp protecting groups both at low and high pH is examined. The Royal Society of Chemistry 2000.
