Ketone hydrosilylation with sugar silanes followed by intramolecular aglycone delivery: an orthogonal glycosylation strategy.
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.
Buchan
Zachary A
ZA
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109-1055, USA.
Bader
Scott J
SJ
Montgomery
John
J
D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D006031:Glycosylation; D007659:Ketones / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*
D002241:Carbohydrates; D007659:Ketones; D012821:Silanes