202401-18-1Relevant articles and documents
Sugar migration induced by the Wagner-Meerwein rearrangement of 28-O-glycosyl-betulin derivatives
Korda, Anna,Pakulski, Zbigniew,Cmoch, Piotr,Gwardiak, Katarzyna,Karczewski, Romuald
, p. 1740 - 1744 (2017/03/08)
Treatment of betulin-type saponins, in which the sugar moiety is connected at the 28-position, with TMSOTf affords 3-O-substituted allobetulin saponins. This unprecedented migration of the sugar part is driven by the Wagner-Meerwein rearrangement of the betulin core. According to our mechanistic studies an oxocarbenium ion released during the rearrangement reacts with the free 3-OH group of the triterpene affording the final allobetulin saponin. Migration rate depends on the size and configuration of the sugar moiety.