T. Khwaja, C. Reese
1971
Citations
0
Influential Citations
16
Citations
Journal
Tetrahedron
Abstract
Abstract Reaction between o-phenylene phosphorochloridate (I) and the 2′,3′-O-isopropylidene derivatives of adenosine, N6,N6-dimethyladenosine and uridine gave, after aqueous work-up, the corresponding 5′-o-hydroxyphenyl phosphate esters (VII) in good yields. Acidic hydrolysis followed by Br2-aqueous bicarbonate oxidation of the adenosine derivatives (VII; B = IXa and IXb) gave the corresponding 5′-nucleotides; in the case of the uridine derivative (VII; B = X), two additional steps were necessary. Thymidine 5′-o-hydroxyphenyl phosphate (XII) has also been prepared. The reactions between the anion of o-phenylene phosphate (V) and the 2′,3′-O-isopropylidene derivatives of adenosine and uridine have been investigated. The main products obtained by heating the 5′-o-hydroxyphenyl phosphates of adenosine and uridine (VIII; B = IXa and X, respectively) in anhydrous pyridine solution have been identified.