Nucleosides. Part VIII. Glucosides of uracil and thymine and the O→N-glycosyl rearrangement

Abstract

By varying the conditions of reaction between the silver salt of uracil and 2,3,4,6-tetra-O-acetylglucopyranosyl bromide (ABG) and from a study of the rearrangement of uracil O(2)O(6)- and N(3)O(6)-bisglucosides it has been shown that these compounds are intermediates in the formation of the uracil N-glucosides, and that a competitive route must exist for the formation of uracil N(3)-glucoside. In the case of thymine, the formation of the N(3)-glucoside from the O(2)O(6)-bisglucoside via the N(3)O(6)-bisglucoside is confirmed.