title: Synthesis of cyclopropyl glycosides and their use as novel glycosyl donors.
abstract: Methods for the synthesis of cyclopropyl glycosides and their use as glycosyl donors are described. Cyclopropyl glycosides containing different substituents were prepared by cyclopropanation of the corresponding vinyl glycosides, or by glycosidation of cyclopropyl alcohols that are synthesized by the Kulinkovich reaction. 1-Methyl- and 1-phenyl-substituted cyclopropyl glycosides undergo coupling to Fmoc-protected serine and threonine and to partially protected monosaccharides in the presence of TMS triflate to give glycosidated products.
authors.affiliation: Department of Chemistry, Villanova University, Villanova, PA 19085, USA.
authors.forename: Clark
authors.initials: C
authors.lastname: Scholl
authors.forename: Thomas
authors.initials: T
authors.lastname: Licisyn
authors.forename: Christopher
authors.initials: C
authors.lastname: Cummings
authors.forename: Kevin
authors.initials: K
authors.lastname: Hughes
authors.forename: David
authors.initials: D
authors.lastname: Johnson
authors.forename: Walter
authors.initials: W
authors.lastname: Boyko
authors.forename: Robert
authors.initials: R
authors.lastname: Giuliano
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D005449:Fluorenes / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D008698:Mesylates / Q000737:chemistry; D009005:Monosaccharides / Q000737:chemistry; D012694:Serine / Q000737:chemistry; D013237:Stereoisomerism; D013912:Threonine / Q000737:chemistry
chemical_list: D000438:Alcohols; D000596:Amino Acids; D003521:Cyclopropanes; D005449:Fluorenes; D006027:Glycosides; D008698:Mesylates; D009005:Monosaccharides; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D013912:Threonine; D012694:Serine; C030797:cyclopropane; C012077:trifluoromethanesulfonic acid