4-N-酰基胞嘧啶核苷衍生物的水热脱酰胺反应：尿嘧啶核苷酯的高效合成

Hydrothermal deamidation of 4-N-acylcytosine nucleoside derivatives: efficient synthesis of uracil nucleoside esters.

作者信息

Nowak Ireneusz, Robins Morris J

机构信息

Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.

出版信息

Org Lett. 2005 Oct 27;7(22):4903-5. doi: 10.1021/ol0518378.

DOI:10.1021/ol0518378

PMID:16235918

Abstract

[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.

摘要

[反应：见正文] N,O-过酰化胞苷和2'-脱氧胞苷衍生物在过热的水/二甲醚溶液（125℃油浴）中发生水解脱酰胺反应（和/或N-脱酰基反应）。源自芳基羧酸的酰化起始原料能顺利得到相应的尿苷酯，并且这类衍生物能从冷却的反应混合物中选择性结晶，产率很高。