A. Schoffstall, H. Tieckelmann
1966
Citations
0
Influential Citations
2
Citations
Journal
Tetrahedron
Abstract
Abstract Dicyclopropylcarbinyl phosphorochloridate has been synthesized for use in phosphorylation reactions. This reagent and primary or secondary alcohols gave the corresponding esters. It reacted with primary and secondary hydroxyl functions of nucleosides to form nucleotide triesters. Dicyclopropylcarbinyl methyl phosphate was hydrolyzed by aqueous acid to monomenthyl phosphate. The nucleotide tristers gave free nucleotides in amounts reflecting their labilities in acid, Thus, uridine-5′ phosphate was produced in 53% overall yield from 2′,3′-isopropylidene-uridine, whereas thymidine-3′ phosphate was obtained in only 12% from 5′-O-tritylthymidine.