2-Cyanoethyl N,N-diisopropylchlorophosphoramidite

Slightly Hazy Yellow Liquid

A protecting reagent in DNA synthesis. Also a phosphorylating agent

2-Cyanoethyl diisopropylchlorophosphoramidite is a useful intermediate in organic synthesis. It acts as a protecting reagent in DNA synthesis. It is involved in the selective monophosphorylation of carbohydrates and nucleosides. It plays an essential role in the conversion of protected ribonucleosides to phosphoramidites. It is also utilized as phosphitylating reagent for 3'-hydroxyl groups in the synthesis of oligodeoxyribonucleotides.

Under argon protection, N,N-diisopropylethylamine ( 1eq ) was added to a stirred solution of dry 1 -butyl-3 -methylimidazolium bis[ (trifluoromethyl)sulfonylimide] in ionic liquid ( 1 eq ) and PCl3 ( 1 eq ), and then the above mixture was stirred vigorously for 5 min, followed by the addition of 3 -hydroxypropionitrile ( 1 eq ). The reaction mixture was stirred for 30 min, then diisopropylamine ( 2 eq ) was added to the above mixture, and the reaction was continued for 40 min with stirring before the reaction mixture was extracted with dry ether, the ether layer was separated, and the corresponding product was stabilized by the addition of 1-ethyl-3-methylimidazolium tris (pentafluoroethyl) trifluorophosphate ( [ C2mim ] [ FAP ] ) into the organic layer, and the product was concentrated under vacuum to remove the organic solvent. The target product molecule 2-cyanoethyl N,N-diisopropylchlorophosphoramidite was obtained by concentrating under vacuum to remove the organic solvent.