M. Miyaki, B. Shimizu
Apr 25, 1970
Citations
0
Influential Citations
18
Citations
Journal
Chemical & Pharmaceutical Bulletin
Abstract
The N-3→N-9 ribosyl (hydrogen halides or mercuric halides catalyzed) migration of N6-acyl derivatives of 3-β-D-ribofuranosyladenine and its 5'-phosphate and 3-β-D-glucopyranosyladenine was found to occur by an intermolecular mechanism. Furthermore, formation of the 3-and 9-ribosyl derivatives was confirmed in the ribosylation reaction of N6-benzoyladenine or its chloromercuri salt using milder conditions. These facts, contrary to the reports which described that the 9-glycosyl derivatives alone could be isolated, suggest that the reaction of N6-benzoyladenine or its chloromercuri salt with glycosyl halides result in the initial formation of the 3-glycosyl derivatives followed by rapid conversion to the thermodynamically more stable 9-glycosyl derivatives in the presence of hydrogen halides or mercuric halides.