title: Synthesis of C-aryl and C-alkyl glycosides using glycosyl phosphates.
abstract: [reaction: see text] Mannosyl and glucosyl phosphate donors were successfully used in constructing C-aryl linkages common to many natural products via a Lewis acid induced Fries-like rearrangement. The rearrangement was stereo- and regiospecific, yielding only one C-glycoside product. C-Alkyl glycoside carbohydrate mimetics were generated by using silicon-derived C-nucleophiles and glycosyl phosphates.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
authors.forename: E R
authors.initials: ER
authors.lastname: Palmacci
authors.forename: P H
authors.initials: PH
authors.lastname: Seeberger
mesh_terms: D015195:Drug Design; D006027:Glycosides / Q000138:chemical synthesis*; D018716:Molecular Mimicry; D013329:Structure-Activity Relationship
chemical_list: D006027:Glycosides