Hydrothermal deamidation of 4-N-acylcytosine nucleoside derivatives: efficient synthesis of uracil nucleoside esters.
[reaction: see text] N,O-Peracylated cytidine and 2'-deoxycytidine derivatives in superheated water/DME solutions (oil bath at 125 degrees C) undergo hydrolytic deamidation (and/or N-deacylation). Acylated starting materials derived from arylcarboxylic acids give the corresponding uridine esters cleanly, and such derivatives crystallize selectively from the cooled reaction mixtures in high yields.
Nowak
Ireneusz
I
Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.
Robins
Morris J
MJ
D000215:Acylation; D003596:Cytosine / Q000031:analogs & derivatives / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013696:Temperature; D014498:Uracil / Q000031:analogs & derivatives / Q000138:chemical synthesis*
D004952:Esters; D009705:Nucleosides; D014498:Uracil; D003596:Cytosine