725223-47-2Relevant academic research and scientific papers
Solution stability and degradation pathway of deoxyribonucleoside phosphoramidites in acetonitrile
Krotz, Achim H.,Rentel, Claus,Gorman, Dennis,Olsen, Phil,Gaus, Hans J.,McArdle, James V.,Scozzari, Anthony N.
, p. 767 - 775 (2004)
The impuritiy profiles of acetonitrile solutions of the four standard O-cyanoethyl-N,N-diisopropyl-phosphoramidites of 5′-O-dimethoxytrityl (DMT) protected deoxyribonucleosides (dGib, dAbz, dC bz, T) were analyzed by HPLC-
Stereoselective synthesis of alkylphosphonates: A facile rearrangement of cyanoethyl-protected nucleoside phosphoramidites
Ravikumar, Vasulinga T.,Krishna Kumar
, p. 603 - 608 (2004)
Cyanoethyl-protected nucleoside phosphoramidites undergo a facile Michaelis-Arbuzov reaction upon addition of acrylonitrile to afford cyanoethyl phosphonates. This rearrangement is stereoselective at room temperature, but racemization is observed at high temperatures, indicating two different pathways. A plausible mechanism is proposed for this reaction.
