Strain-Assisted, Unusually Facile Hydrolysis of the Nitrogen-Bridge of a Tricyclic Uracil N-Cyclonucleoside

Autor: Minamoto, Katsumaro, Azuma, Kishiko, Hoshino, Yorihisa, Eguchi, Shoji
Zdroj: Chemistry Letters; May 1989, Vol. 18 Issue: 5 p825-828, 4p
Abstrakt: With respect to “up” amination of the sugar part of nucleosides through an appropriate N-cyclonucleoside, 5′,N-anhydro-2,2′-imino-1-(2′-deoxy-β-D-arabinofuranosyl)uracil proved to be easily hydrolyzed to 1-(2′,5′-N-anhydro-5′-amino-2′,5′-dideoxy-β-D-arabinofuranosyl)uracil (2) in dilute alkaline or acidic medium. 2was characterized as its acetylimino analogue or hydrochloride, and proved to trans form to 5′,N-anhydro-6,2′-imino-1-(2′-deoxy-β-D-arabinofuranosyl)-5,6-dihydrouracil spontaneously.
Databáze: Supplemental Index