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Ketone Hydrosilylation with Sugar Silanes Followed by Intramolecular Aglycone Delivery: An Orthogonal Glycosylation Strategy
Buchan, Zachary A.; Bader, Scott J.; Montgomery, John
Buchan, Zachary A.; Bader, Scott J.; Montgomery, John
2009-06-15
Citation:Buchan, Zachary 14A.; Bader, Scott 14J.; Montgomery, John (2009). "Ketone Hydrosilylation with Sugar Silanes Followed by Intramolecular Aglycone Delivery: An Orthogonal Glycosylation Strategy We acknowledge support from the National Institutes of Health (GM 57014) and from Thermo Fisher for a pilot project grant administered by the University of Michigan Life Sciences Institute. ." Angewandte Chemie International Edition 48(26): 4840-4844. <http://hdl.handle.net/2027.42/63086>
Abstract: Gettin' a little sugar—no alcohol required : A procedure for the direct glycosylation of ketones without a hydroxy intermediate enables the site-selective glycosylation of hydroxyketones at the ketone or the alcohol functionality without the use of protecting groups on the aglycone (see scheme). Site selectivity is controlled by the catalyst structure in hydrosilylation and dehydrogenative silylation reactions with sugar silanes. Bn=benzyl.
