321ChemInform Abstract Acetonation of lactose (I) with excess 2-methoxypropene (II) under the conditions indicated in the scheme yields two products which are acetylated and isolated as the anomeric mixtures (III) and (IV) (no yields given). 1H NMR data reveal that the diacetal formed in this reaction has structure (III) and not, as previously reported, structure (V). Furthermore, the reaction method is investigated forsome lactosides, especially for benzyl lactoside. In all cases, retention of the interglycosidic linkage is observed. In order to test the synthetic utility of kinetic acetonation, the chiral macrocyclic ether (VIII) is prepared in a one-pot procedure from the lactoside (VI).
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.