title: Formation of 1,1-alpha,alpha-glycosidic bonds by intramolecular aglycone delivery. A convergent synthesis of trehalose.
abstract: [reaction: see text] We report a new synthesis of trehalose analogs that involves the use of intramolecular aglycone delivery for stereoselective formation of the 1,1-alpha,alpha-glycosidic bond. The glycosylation reaction afforded the desired isomer exclusively and in good yield.
authors.affiliation: Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720-1460, USA.
authors.forename: Matthew R
authors.initials: MR
authors.lastname: Pratt
authors.forename: Clifton D
authors.initials: CD
authors.lastname: Leigh
authors.forename: Carolyn R
authors.initials: CR
authors.lastname: Bertozzi
mesh_terms: D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D007536:Isomerism; D008956:Models, Chemical; D008969:Molecular Sequence Data; D010084:Oxidation-Reduction; D014199:Trehalose / Q000138:chemical synthesis*
chemical_list: D006027:Glycosides; D014199:Trehalose