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Ketone Hydrosilylation with Sugar Silanes Followed by Intramolecular Aglycone Delivery: An Orthogonal Glycosylation Strategy
Author(s) -
Buchan Zachary A.,
Bader Scott J.,
Montgomery John
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200901666
Subject(s) - aglycone , hydrosilylation , silanes , glycosylation , chemistry , ketone , intramolecular force , silylation , organic chemistry , selectivity , sugar , alcohol , catalysis , glycoside , biochemistry , silane
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.