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Isopropyl and p-nitrophenyl α- and β-d-glucopyranosides, restrained in a conformation close to B 2,5 via an oxymethylene bridge have been synthesized. These four glucopyranosides were found to be hydrolyzed at similar rates, close to those observed for the parent unconstrained glucosides. In such derivatives, either α or β, the exocyclic cleaved bond is synperiplanar to an endocyclic...
Trimethylaluminium induces a stereoselective rearrangement of unsaturated glycosides into polyfunctionalised cyclohexanic rings containing a tertiary alcohol and retaining the anomeric group. In contrast with the previously used triisobutylaluminium, no de-O-benzylation reaction was observed.
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